Sell Or Rent Out My Home? Depends On Your Passive Income Goals

Are you wondering whether to sell or continue renting out your home? I had this same dilemma of sell or rent out my home back in 2016. In the end, I decided to keep my rental property to build more passive income.

Things are strange now with many people buying a home during the coronavirus pandemic. It's almost kind of nuts how strong demand is due to record-low mortgage rates.

Maybe you're thinking about selling your home because you think the market is going to crash. Or maybe you want to sell your home to upgrade your lifestyle since we're all spending more time at home now.

Whatever the case may be, the question to sell or rent out my home is one that many people are wondering right now. Real estate is one of my favorite ways to generate passive income for financial freedom. Once you sell your home, you lose a good income source.

Let me share with you my own situation to sell or rent out my home as it may help you better decide as well.

The Sell Versus Continue Renting Dilemma I Faced

2016 was supposed to be the year where I'd finally achieve my passive income goal of $200,000. The goal was first established in 2012 when my passive income machine was generating about $80,000.

I figured, if I could find a way to generate $200,000 a year by 2015, life would be good and I'd never have to work in the salt mines again. In 2015, I came up $25,000 short. Now it looks like I'm going in reverse! What the hell is going on?!

As fate would have it, just a couple weeks before my business trip to Europe, my tenants gave me their 30-day notice on a rental that is generating $4,000/month.

After all expenses, the property nets around $3,000/month or $36,000 a year. This rental has been a champ with not a single month of vacancy since its 2005 deployment.

Now I'm faced with a decision. Do I try and find new tenants or sell the property in what appears to be a weakening real estate market. Maybe you will face this dilemma one day. Let's discuss some considerations to make the best decision possible!

Sell Or Rent Out My Home?

The older I get, the more I want to simplify my life. When I was working full-time, I used to love real estate. During my darkest corporate hours, real estate was the main HOPE that would allow me to one day break free. I didn't care about doing house calls when things broke.

I didn't mind going to the yearly HOA meetings. Hosting open houses was fun because I could meet all sorts of people who shared fascinating details about their lives. I knew that every action brought me closer to financial freedom.

Since escaping my employer with a severance, however, I have slowly become less interested in landlording. Every text message from a tenant with a problem or every flaker at a open house bums me out.

Due to my severance that is still paying out today, the plan to live off my passive income did not materialize. In fact, since I left work pretty much all my passive income has either been saved or reinvested.

Then starting in 2014, I rented out my old house because I downsized to a fixer in a quieter neighborhood. With two rental properties to manage plus a vacation property, I became even less satisfied with landlording.

Although I have a lot of free time, landlording started feeling like a job, which is completely opposite of why I wanted to retire early! And what bums me out most is tenants agreeing to lease terms and then breaking the lease terms. Why can't everybody just do what they promise?

Catalyst For Wanting To Sell

The final thing that's really made me consider selling is the unexpected growth of my online business. I'm having so much fun being an entrepreneur, that I'm finding I don't really want to bother with real estate anymore. I've always preferred having fun and making money on the side rather than making money and eking out some fun.

My layoff strategy guide alone makes around the same amount as my rental property. Further, the book requires no maintenance or ongoing tax on its value. It's about as passive an income stream there is. I've got a pretty fun post in the pipeline which compares real estate and an internet business you won't want to miss.

But the real reason why I thought about the sell or rent out my home question was because we were having our first child in 2017!

The last thing I wanted to do as a new father was manage tenants and maintenance issues. As a result, I ended up selling our home.

Always Do The Math When Deciding To Sell Or Rent

To determine whether to sell or rent your home, always do the math.

Now that I've shared my subjective feelings, I'd like to focus on objective numbers. At the end of the day, an asset's value is based on the cash flow it can provide.

Not continuing to rent out the property means roughly $36,000 in lost income. Due to depreciation, the taxable income is actually much less. Not all is lost, however, because selling the property would yield proceeds that can be reinvested.

Nobody knows exactly what they will get for their property until they finally get some offers. But you can make educated guesses about a price range you will likely receive by comparing the comps that recently sold based on price/sqft and using cap rates.

Analyze The Comps

My property is 1,000 square feet. Recent comps have sold for $980 – $1,500/sqft in the Pacific Heights neighborhood. Therefore, the range is $980,000 – $1,500,000. Anything above $1,300/sqft is a prime property that has been remodeled.

The only thing that has been remodeled in my condo is a bathroom. Everything else is original since 1980. But, I've got an amazing dead on view of the park. Therefore, my educated guess is somewhere around $1,100 – $1,200 / sqft, or $1.1M – $1.2M.

Please don't get hung up about the price of property here in San Francisco. It's expensive here. Focus on the methodology.

Use A Realistic Cap Rate

Now turn into an investor and use a capitalization rate (cap rate) to value your property. Take your annual Net Operating Income (gross rents minus property taxes, maintenance, HOAs, etc) and divide it by a cap rate in your region. Think about a cap rate as the required rate of annual return on the property or the rate of return buyers in your area are willing to accept.

For example, if you accept a low cap rate of 2%, you believe the property is in a rock solid area and has a strong chance of appreciating. Therefore, income is a secondary consideration to appreciation. If you accept a high cap rate of 10%, it means there's probably little chance of strong capital appreciation, so you want higher income now.

In San Francisco, the cap rate is currently around 3.8%. That's 2% higher than the 10-year bond yield, also known as the risk free rate of return.

If I want to drill down even further, I need to calculate the cap rates in Pacific Heights. If SF's cap rate is 3.8%, then Pacific Heights' cap rate must be between 3% – 3.7% in my opinion.

Related: How To Properly Analyze And Evaluate A Rental Property

Find Out Where The Two Values Intersect

To determine whether to sell or rent a home, take your annual Net Operating Income and divide it by your area's estimated cap rate. In my case, I would take $36,000 / 3% – 3.7% = $973,000 – $1,200,000. I can take the average and get $1,086,500. 

Now I compare the cap rate calculation value to the comps and focus on the overlap. The realistic selling price is therefore around $1.1M. Anything more than $1.1M should be considered a win. Anything less requires more deliberation.

Identify The Special Features Of Your Property

Every property has its intangibles that might sway people to bid much higher than the numbers dictate. I place a premium on properties with views.

This property has fantastic park views. I would have happily paid at least $50,000 more for the property when I first stumbled across it for $580,000 back in 2003.

But some people like to face other buildings and would never pay a premium for having their eyeballs massaged after work everyday. You just need to find that one buyer who places a premium on what your property offers to get top dollar.

It's very easy to get biased about our own properties. Selling this condo is like selling my baby since it was the first property I bought as a 25 year old.

Being delusional about your property's shortfalls is hazardous when it's finally time to negotiate a selling price. Remember to treat your assets as a means to an end. My end has always been happiness and freedom.

Future Income On Sale Proceeds

Let's say this property sells for $1,120,000. After fees and taxes, I'm left with around $1,000,000 since there is no mortgage on the place. What can $1,000,000 generate based on what I want to invest in? Here are some reinvestment ideas after a home sale.

1) 5-year CD at 2%: $20,000 a year. Shortfall to existing income generation: $12,000.

2) California muni bonds at 2.5%: $25,000 a year tax free. Shortfall: $11,000. Don't think California will default.

3) High Yield Dividend ETF (DVY): $36,000 a year in dividend income. No shortfall, but potentially lots of principal risk.

4) Venture Debt fund with target IRR of 16%: $120,000 a year for a total return of $840,000 over seven years if I assume a more modest 12% IRR. But there's probably a 30% chance of losing $200,000 at the end of the fund.

5) Automatic investing: I could choose a very conservative risk tolerance and have a robo-advisor automatically invest a lump sum or new funds every month into a 50/50 equities and bond portfolio with a 2.5% yield to generate $25,000 a year in gross income.

6) Diversify into real estate crowdfunding. One of the best ways to make passive income is by investing in publicly traded REITs or less volatile private REITs offered by Fundrise. Fundrise offers a very diversified portfolio of eREITs or eFUNDs so investors can invest in real estate across the nation. It's free to sign up and explore.

Rent or sell my home? Invest in passive real estate

As a father of two kids now, investing in real estate crowdfunding has been a great alternative. I now earn real estate income 100% passively, which is what I want since time is so precious nowadays.

Another great platform if you want to invest in individual commercial real estate deals and are an accredited investor is CrowdStreet. CrowdStreet focuses on individual deals in 18-hour cities, where valuations are lower and cap rates are higher.

The Final Question To Ask Before Selling Or Renting Out Your Home

Deciding on whether to sell or rent out your home is tough.

I believe everybody should own property for as long as possible. The 5% commission rate and the taxes on profit are economic leaks. Given inflation is almost always up and to the right, your property should keep up over the long run. You want to build as much passive income as possible for financial freedom.

But if you just can't take landlording anymore, don't want to hire a property manager, and believe the timing is right, then selling is a good solution.

The final question you should ask yourself before selling is, “Will I be kicking myself 20 years from now for selling today?” If you're over the age of 60 with a pension that provides for all your needs, who cares? Life expectancy is only about 84. You might gain a great deal by simplifying the remaining 24 years of your life.

If you're still working towards your financial nut, don't have any other income streams, don't really like your job, and aren't willing to start a side business, your property might be one of the few things keeping your hopes alive. It often takes several years of losses before finally breaking even. Be patient enough to let inflation make you whole.

The other thing to think about is what will your children in the future think of your decisions today? In 30 years from now, will they think you were smart or dumb for selling a home today?

If history is any guide, chances are high that in 30 years, our children will be impressed you bought real assets today. If you didn't buy, then at least you held on.

Latest Passive Income Chart

Below is my latest passive income chart that enables my wife and I to be stay at home parents to our two little ones. We plan to continue building our portfolio so we can remain financially free.

I ultimately decided to keep my SF rental condo. It's paid off and generates $4,200 a month. The condo faces a park in Pacific Heights and is a great passive income source.

However, in 2017, I did end up selling my SF rental house for 30X annual gross rent ($2,740,000) to simplify life. I didn't want to deal with tenants who kept throwing parties and breaking things. As a first time father in 2017, I was happy to sell my home.

I reinvested $550,000 of the proceeds in real estate crowdfunding and the rest in stocks and municipal bonds. It feels so much better to passively earn income. 

Financial Samurai 2021 Passive Income Streams


Explore real estate crowdsourcing opportunities: If you don't have the downpayment to buy a property, don't want to deal with the hassle of managing real estate, or don't want to tie up your liquidity in physical real estate, take a look at Fundrise, one of the largest real estate crowdsourcing companies today.

Real estate is a key component of a diversified portfolio. Real estate crowdsourcing allows you to be more flexible in your real estate investments by investing beyond just where you live for the best returns possible.

For example, cap rates are around 3% in San Francisco and New York City, but over 10% in the Midwest if you're looking for strictly investing income returns. Sign up and take a look at all the residential and commercial investment opportunities around the country Fundrise has to offer. It's free to look.

Refinance your mortgage: Check out Credible, my favorite mortgage marketplace where prequalified lenders compete for your business. You can get competitive, real quotes in under three minutes for free. Mortgage rates are down to all-time lows! When banks compete, you win. 

If you can refinance your mortgage and lower your carrying cost, it makes owning a home that much easier. I refinanced in 2019 to 2.625% for a 7/1 ARM and rented out the home in 2020. In 2020, I decided to take advantage of softness in higher-end property and buy a new home. I got a 7/1 jumbo ARM for under 2.35%.

About The Author

163 thoughts on “Sell Or Rent Out My Home? Depends On Your Passive Income Goals”

  1. I read with great interest the decision strategy by Vicki a few minutes ago, and now have curiosity to know what Sam decided to do? Sell or keep the home (property)?

  2. You have a good nose for real estate. I was wondering what your opinion is on northern Colorado. Seems to be one of the hotter real estate markets. Seems like there is an argument that prices will level out or maybe even retract? Is this wishful thinking? We currently rent, and are waiting for the right time to buy a house. We then may turn it into a rental 3-5 years down the road.
    The fed is indicating that they will raise the fed rate 3 times in 2017. What does that mean to the market? Will realestate slow down? Will there be a frenzy before rates really rise? Are the values in Northern Co way overvalued. From what I can tell from my random research. Prices seems to be 10-15% over fair value. However we all know “fair value” doesnt mean squat. It could be 50% over in a year or two if things continue.
    Lastly, I found that in the past, real estate doesn’t go down when rates go up…unless its a quick spike. It seems that suppy and demand trump the cost of borrowing money.
    Great blog much appreciated.

    1. Hi Arik,

      Check out these posts:

      Should I buy a home in a rising real estate environment – this one should help you think about things more

      Buy real estate as young as you possible can

      Prices are softening in coastal cities, and slowing down in places like Denver. I don’t think there is any rush. There’s ALWAYS another great property to be had if you miss one.

      In the meantime, I’m investing more surgically in the heartland of America (South, Midwest), where returns are greater, through a real estate crowdsourcing platform called RealtyShares. I just made a $25,000 investment in Austin, Texas this weekend, and plan to do more.


  3. hey Sam, when you say you have close to $200k passive income, what is the actual net amount?
    You have a few properties which have mortgages I assume. You rent out your SF house for $9k/month, that’s about $100k per year.

    With all housing related costs (mortgage, insurance, taxes etc…) it’s very different from earning say $10k in dividends which is mostly tax free.

    200k no doubt is a very impressive number, just that it’s skewed because of operating costs.

  4. I just sold my triplex that I bought at 26, circumstances were a little different but I made the call to lock in the win. I’m a realtor in Southern California and I think we’ve definitely got the economic speed wobbles. I’m betting on the next crash being super bad and think that having the cash on hand to take advantage is worth paying the capital gains tax (still feels like the government is mugging me though). That being said, it sucks just sitting on the money for now, but I want it liquid just in case. Also, been reading your stuff for a couple of years now, really love the site! Thanks for all the great ideas and analysis!

    1. The downward pressure has already begun! Lower rents are great for people will will have more disposable income to spend and help the economy. More workers would be hired as well, driving back prices. I do feel tech companies have been a boon for landlords, and if they can pay the same or more to help displaced residents find affordable housing, great. I just don’t know whether the money will be used as intended.

      What do you think?

      1. Probably on the margin I think it would hurt rental incomes – it probably depends on how many properties they actually build, how big the units are, and what they actual charge tenants for them. Probably would be more “pain” at the low end of the rental market than middle and higher end.

  5. What about Capital Gains taxes due on the sale…How do sale proceeds on a long term investment that are $1,000,000 not get taxed?

  6. Warren Franklin

    Sam, hold on to the property and get a property manager if dealing with the tenants is too much. in the long term you will be happy with the decision.

  7. That’s a pretty terrible ROI on rental property. I’m not sure I’d invest in rental properties in San Francisco.

    I make $25,000/year on a $425k house. I have a few other properties as well. Generally I buy properties in the $125k range and clear about $10,000/year on them. Rent of $1350/mo – fees around $500 (HOA and taxes are just $400/mo and figure $1,000+ in maintenance). On $1.2M, I’d expect to earn upwards of $75k/year.

    I guess the decision is really about where you want to live. Because you can do much better in a different area with real estate.

    What I have done is link up with a few good professionals and services. Appliance goes out? I know exactly who to call. They schedule with tenant and deal with it. Tenant moving? My realtor knows what to do. My actual effort is minimal, maybe a phone call or two a month – and that’s with 5 properties.

    1. Indeed. Cities like San Francisco, Manhattan, London, Hong Kong, etc have very low cap rates. Instead, people buy property for lifestyle and capital appreciation.

      Prices are supposedly up about 68% since 2012. So if you have a $1M property in 2012, that’s a nice $680,000 + the $40,000 – $60,000 in gross rent you are making.

      Where do you live and buy and how long have you owned?

      1. I’ve been off/on reading your stuff. I really enjoy your writing. As my business has done so well, I’ve been looking for more financial strategies and ideas.

        Anyways, you have seen a better ROI simply based on the property value in San Francisco. But that only works when you sell it. I would expect rents to go up accordingly, and always thought they did, but it’s interesting that it doesn’t seem to be the case when hearing about your experience.

        I own property in South Florida. I’ve started acquiring property about 4 years ago as my business boomed. Not knowing the future, I wanted to own free and clear property for financial security. So I bought 3 properties in the $120k range, and that income paid the mortgage on my primary. Then business kept doing so well, I paid off the primary and moved up to a bigger primary. So now I have 4 rentals and a primary.

        I’m not sure if it’s the best approach, but it works for me. I know that I have an amazing house, paid off, in a great area/school district (I have 2 young children), and the income from the other 3 rentals is enough where I technically wouldn’t have to work, but would live semi-frugally. It feels nice having that security. I’m only 32 and I have semi-financial security for my family. It eases anxiety and pressure, that’s for sure.

        I think the “smart money” might say to sell in San Francisco and buy elsewhere with better returns. But as we both know, it doesn’t work that way. I’m sure you love where you are.

        1. Sounds good to me.

          For SF and these other “international cities” is that cap rates have been low e.g. 4% or less for a long, long time. At least since the late 90s when I first seriously started looking.

          Being not having to work at age 32 is amazing. Congrats! I should have bought a Manhattan 2/2 condo in 2000. I might have been able to be financially independent by 32 too! The place was around $800,000 and is probably worth around $2.4M today.

    1. I saw that article. Good to see rent and prices have gone up 6.6% a year on average for 60 years. I’ll take that, b/c my goal is for a 4% net worth increase each year compared to inflation of around 2%.

      You can’t build fast enough in SF due to zoning, so holding for the long term is generally a great idea. I’m leaning towards holding on and just leaving my place empty until I find the right tenant. No more need to rush to get 100% occupancy anymore.

      1. I’ve been following the conversation and must jump in here to help solve your dilemma. Since you say the work involved in getting the place ready for another renter was the trigger event, and now you would just as soon leave it empty, I’d offer to condo sit and do the physical labor required just to get to leave yucky Houston and stay in a nice SF condo for FREE. I’m an artist and retired from public ed., which means I’ve been through an FBI clearance if that gives you any assurances I’d be an honest worker/tenant who would cost you zero dollars and leave the condo looking great. I’ve considered a trip to Italy in one of those free rent in exchange for farm labor arrangements but I’m actually more of a city girl. Just thought I’d throw out the idea. Now, I wouldn’t offer this for just any condo. I saw the photo at the beginning of the thread and if that’s the condo I’d fuss over every little detail of that beauty like it were my own and be there to show to prospective renters for at least a month…

      2. I’ve been following the conversation and must jump in here to help solve your dilemma. Since you say the work involved in getting the place ready for another renter was the trigger event, and now you would just as soon leave it empty, I’d offer to condo sit and do the physical labor required just to get to leave yucky Houston and stay in a nice SF condo for FREE. I’m an artist and retired from public ed., which means I’ve been through an FBI clearance if that gives you any assurances I’d be an honest worker/tenant who would cost you zero dollars and leave the condo looking great. I’ve considered a trip to Italy in one of those free rent in exchange for farm labor arrangements but I’m actually more of a city girl. Just thought I’d throw out the idea. Now, I wouldn’t offer this for just any condo. I saw the photo at the beginning of the thread and if that’s the condo I’d fuss over every little detail of that beauty like it were my own and be there to show to prospective renters for at least a month…

  8. I think one problem and asset you have is your financially at the finish line, where most readers are not. You got a lot of dough to maintain your life, but now your biggest problem is not screwing up what u already have.

    Your relevant investment thinking and decisions and sharing those creatively is what keeps your fine edge samurai sword sharp and why people read and hopefully you enjoy doing it as much as we enjoy reading.

    I think your biggest risk in the sf property is lack of diversification for such a large amount of $.
    Your return is fairly low to compensate you for keeping your wealth in one place also sounds like you have another property in same geographic location. I would sell and put my money in pockets where I could not lose in one big swoop. Maybe buy real estate in different locations and that would still be all in real estate if you think that is the safest. New homes have less headaches. If you decide on property management I bet with your skill you could cut a solid deal that would make you more money, and less hassle.

    I am sure you checked with your accountant too. I always try to live for 2 years in my home before selling. Yes you still have to pay back the depreciation you took renting, but sometimes still advantageous to move in and sell or sell primary property.

    With no crystal ball no clear cut absolutes around for returns, the closest we have is that the feds can’t let housing or the stock market crash because it could be unrepairable. but low interest rates and helicopter money for long term seems to be what is easiest to give.

    1. I’m exploring new reinvestment opportunities if I sell the condo, but will only sell the condo based on a minimum price. Otherwise, the rental market is so strong in SF that I’ll just keep the cash flow forever.

      Here’s a new option I just wrote about:

      I believe we’re going to go in a 2 year existing home sales lull as incomes try and catch up to price increases.

      What’s your story?

  9. You have a 2 bedroom condo in Pac Heights that’s making you a significant amount of money. Unless you’re withdrawing from the San Francisco market altogether, hold onto it. Your tax base is super low and you would literally have to pay double the property taxes on an equivalent unit should you change your mind after selling.

    BTW, I thought you wanted to accumulate more SF real estate, based on your previous posts, no? Sounds like you’re going through a period of re-evaluation of your priorities. Take your time…a month or so of vacancy is not the end of the world.

    1. Weird how things change when there is a trigger event isn’t it? Sure, I’d love to keep the condo if there was nothing to do. But once work is involved, it’s easy to have a change of heart.

      Weird how things change when there is a trigger event isn’t it? Sure, I’d love to keep the condo that there was nothing to do. But once work is involved, it’s easy to have a change of heart. The more I think about it and read the comments, the more I’m at peace with holding onto it.

      If I have to pay 20% tax on a $500,000 profit, I might as well just not even rented for two years and establish residency there to save on taxes right? I would forgo the same $100,000 in expenses As rent. Or am I missing something here?

  10. cameljockey

    While you clearly don’t enjoy the prospect of obtaining new tenants, it’s a short-term issue. I think the real problem is that you have too much cash locked up into an investment with poor returns. Why not take a HELOC and invest in Prosper loans or other relatively passive investment vehicles where you can make money on the arbitrage between artificially low rates on the money you borrow versus the rate of return you can secure from the alternative investment. This obviates the needless cost of paying a broker commission/taxes, etc.. You would make money on the rental as well as on the other investment, and could probably deduct the interest you pay from your taxable income.

    1. I’ve pretty much found my enough number, and if the enough number can grow at about 4% a year, I’m getting 4% more than enough every year. This is why I’ve held on for the past several years now, but now I’m wondering whether to simplify.

  11. Brad Spencer

    Why not take some of that money and invest it into creating a few more digital assets?

    The income generated is EXTREMELY high ROI due to high gross margin of each sale and potential for upsells.

    I want to invest personally into real estate (and it’s what I got my degree in but got creamed in 2008 and had to pivot the last 8 years or so) but I can’t see why a simple “buy and hold” is a good idea in your market.

    The risk of the property dropping by 50% sometime in the next 5 years is a LOT higher than it increasing by the same amount in the next few years. Lock in the gains, sit on some cash, and then if you want to buy again buy once the startup bubble deflates a bit and the market gets bit more rational.

    I mean doubling your digital businesses would be a LOT easier than doubling your real estate cash flow over the next 3-5 years. Waiting 10+ years for inflation to bail you out of a purchase (or not selling at the peak) is too risky in my opinion.

    With your talent and experience, 10 years of optionality by selling your property now while the market is in a peak cycle and then having access to the cash either to reinvest into your digital businesses/assets and also just sit on it to invest into hard assets once things deflate a bit would be a lot more “risk smart.”

    Hope that makes sense.

    Full Disclosure: I’ve been working in the digital product creation world for the last 8 years and it’s getting easier and easier once you have a successful product like yours to add a simple backend and 50% increase your income by solving a “cousin product” to the folks buying your product.

    1. A potential real estate downturn is definitely one of the reasons why I’m considering selling. We’ve seen a huge runup indeed. I think we’ll see a 10-15% softening, and then a flat line for years before an upward resumption.

      What products do you digitally create? The point I’ve alluded to in this post is that my digital business is more profitable and fun than my real estate business. It’s what I mostly want to focus on now.

      The question is, how much is enough? $250,000 a year in operating profits? $500,000? $1M? It never ends, which is why I’m traveling right now for business to mix things up!

      1. Brad Spencer

        Totally dig it :)

        I was speaking with a gentleman who lives near me in the Orlando area and he’s been investing in real estate since the late 1960’s down here and one thing he said throughout the cycles of ups and downs was “never underestimate the power of closing out a big gain.” He had made his 1st million in 1972 when our local government bought part of his orange grove to put a road through it. That was his “big win” that set him up to own various assets and a local bank here.

        Cool story but I’ll never forget how he got “lucky” a few times and he said inflation would’ve taken him another 30 years to make that money he did on that one key sale.

        So all good on the real estate either way but thats what inspired me to vote for selling it :)

        As for digital products, we do mostly 3-4 week classes and then sell the recordings after class is over. I’ve done a lot of other digital products such as product launches with affiliates, higher end (3-5k) phone sales, and more mid-ticket items in the $297-$1k range for people wanting to start businesses. Not the hypey/sleazy stuff obviously but consistent businesses focused on replenishable items sold on Amazon and through people’s own websites (like how you sell your book).

        We mostly talk about dropshipping and wholesaling and are going to be doing more with Amazon’s Pay Per Click marketing services over the next few months.

        As for “enough money,” I don’t know if there’s a number. I think there’s an element of a “video game” that kicks in once you have your number. I’ve made a lot of errors in my 20’s related to buying cars (which is how I originally found your site a few months back when I saw your 1/10th of income car rule post) and not being as focused on systems.

        I as well had a finance background but graduated in 2008 with a focus on real estate finance (mortgages and financing of real estate was what I wanted to do) but that ended up being awful timing.

        So been on the product creation side and building my own things and all that. Lot of fun in my opinion.

        One big thing I’ve taken from you from a “mindset” type perspective is the focus on optionality. That’s been key over the last 6 months and has really lightened my load so appreciate you for that. For me, that means the option to make more and build more assets…or not.

        It’s been fun having that optionality to start and build up more assets in the ways you have as well (I started digital assets and haven’t had a typical corporate job/salary or properties).

        Anyhow…think you have my email on the blog comment…would love to connect with you when you have some time and chat digital assets…it’s the least I can do for all the value you’ve shared here. No rush as I’ll be out of town this week til Sunday but would love to show you a few things and see how you’re promoting your book beyond mentioning it in posts.

        If I can help you out, I’d be happy to :)

        Take care buddy and either way…I appreciate you taking the time to write and share a lot of contrarian perspectives. They’ve helped me out a lot.

  12. Chris Johnson

    Option 1 – 1031 the property into an area with a higher CAP rate, and use the increased cash flow to pay a property manager, to lower your involvement in running the property. To get a higher CAP rate, you might need purchase something out of state. Some upfront time involved in researching the property, and purchasing it, but after that should be minimal effort on the part of the investor.

    Option 2 – Sell, and invest in first mortgage notes. Currently, I invest with a hard money lender that lender that writes Interest Only Mortgages with 8% return to the investor. The hard money lender services the loan, and just sends you a check every month. Principal is secured by underlying equity in the property (unlike Lending Club that is unsecured debt).

  13. I will offer up a strategy for you to consider, since you previously lived in the home and I assume you like it enough to live there again.

    The current state of capital gains tax on housing is that if you have lived in your home for 2 of the last 5 years, you can take a $250k gain exclusion for single or $500k gain for married. It doesn’t matter if you live there the first 2 years of the past 5 or the last 2 years of the last five.

    If you move into the property for 2 years prior to selling and you can potentially pay no capital gains. (downside note, you will have to pay depreciation recapture tax either way…)

    This is not to say I vote for you to sell, just that if and when you are ready, make it a 2 year process in order to get maximum tax benefit from the proceeds. My vote is to keep renting it for 20-24 years, then live in it for 2 years, then sell it for the capital gains exclusion.

    (disclaimer: verify this concept with your own tax advisor, just because it works for me, doesn’t mean you wont get audited later for doing your taxes wrong…)

    1. It’s a good idea, although I think the rules have changed somewhat on the tax free amount.

      I may just leave it empty, or have it be my primary residence as I travel and stuff for two years to get some of that tax free profit back.

  14. Since you already own 2 rental properties plus a vacation home, it might not be a bad idea to take some money off the table given the market is at a high with the median home price for San Francisco crossing $1 million. The San Francisco case-shiller price index at 218.87 for Feb 2016 is pretty much the highest it has been in the past 10 years.

  15. Since you have 2 “risk” free methods that can generate 24-25 thousand a year with the potential money, the question for me would be is $12,000 more worth the hassle of dealing with tenants. To me it wouldn’t be. But that’s up to you. The potential damage tenants could do would eat up that extra in a hurry.

  16. Imvestment Ninja

    I have a home worth $340K at the moment and have over 100K equity. Would it be wise to rent this out and take the equity and use it to buy another single family home? Or take that equity and get me a small cheap property and continue living in the home that I am currently in? Or shall I just take that equity and invest in the market? I have witnessed the trials of having to keep up and maintain rental property. Even with a property manager you have to manage them as well. Not all property managers are in the best interest of you, this goes especially for those of you that depend on them to take care of the work from faraway. When it comes down to Financial Samurai’s decision it is what you value the most. Having a home that you have had for years and going through the process of getting another tenant and receiving the rental income and other risks that come with it. Or selling it and moving on to other forms of investing that are less restrictive such as investing in the market.

  17. I must admit, as a property owner myself who self manages, I also get that knee jerk reaction whenever a tenant vacates – I just want to sell the property, and as I lean towards those thoughts I’m filled with calm. Finding a new tenant, although pretty easy, sometimes I think I can’t hack it anymore. That said, when they are in, that wave of calm comes over me again and I’m glad I didn’t sell.

    A suggestion. I have a girl that works part time for me (self employed, and paid hourly) for managing my properties and it works brilliantly. I only hear from her if there is a problem she can’t sort out. I also have a builder who takes care of any maintenance below an agreed £ amount without bothering me.

  18. I voted sell. The market looks good and you don’t need the hassle which is all I see tenants as.

    We had tenants many years ago. They rented for about 5 years and in that time my parents never raised the rent (because they felt sorry for how little the husband earned), all the while performing maintenance on the house and taking them shopping every month (the tenants didn’t have a car). It was the cheapest two bedroom & tbk in the city with a chaffeur service to boot.

    The tenants paid only for the house (electricity and water was included), so they used to invite the neighbours to cook and use all the water they wanted. When they left, the house was pretty trashed and we had to strip walls and floors.

    But we’re grateful for small favours (that they packed up and left) because the govt. has changed the laws and now if you have a tenant, you can’t kick them out even if they stop paying rent. It is up to the owner to find the tenant an affordable place to their liking!

    Definitely not worth the effort.

  19. Easy.

    Sublet your apartment for a month or two until your trip is over. Then you can find a long term tenant.

    I’d love to have your problem ;)

  20. This is a hard choice. The finances and the desired life outcome are not entirely clear. Approaching it rationally may not be possible. Have your other goals changed? Do you still need/want $200K of passive income a year? Or has your baseline shifted?

    1. I don’t need the $200k passive income anymore. It was just a goal I had in 2012. The reason is my online income grew far beyond what I thought it would grow to. So 100% of the passive income has just been saved. Of course the online business could all go away one day more easily than rental income. Thoughts now?

      1. Hi Sam
        Where are you in Europe? I am in Madrid following 2 weeks in Russia.
        Here’s my POV and what I did related to the decision you are considering.

        Rentals are a hassle when tenants give notice but usually no hassle after the new great tenant moves in. That being said I sold a rental condo a few years ago — condos are way more hassle than single-family dwellings even with a great PM, usually don’t appreciate as much, I can’t stand dealing with the strata corporation and just ignore it, and condo tenants are not as good as SF house tenants.

        I was so glad to put the proceeds into the stock market (income of which is funding my travels for half the year). I quite enjoy managing my own financial investments and I can do that wherever I am. Meanwhile, my house in Vancouver has appreciated astronomically (I will never sell it although it is tempting when I work the numbers they come out on the hold side).

        I still rent 2 smaller units in my house and live in a third unit. This means I can walk away any time to travel as the tenants are there to look after everything. I am extremely picky about tenants — my PM finds them but I always meet them myself. I left one unit vacant for 2 months last year while I was travelling. The income loss was mitigated by lower income tax (expenses remain same).

        Re other sources of income. I find most passions become chores after 5-6 years. You are still going strong, but I can see other great bloggers burning out. I loved my consulting work but after 6 years, I just wanted no commitments. Now my challenges are travel logistics and I meet the most amazing people.

        1. I’m in Prague now, ready to go check out the castle!

          Nice job on Vancouver, a city even hotter than SF it seems! What is he industry making things so expensive? Or is it all foreign money? What is the value of your Vancouver home now?

          I’m not enthusiastic about the stock market currently. But I may just buy California muni bonds with the proceeds.

          What I love is blogging. The upside is massive and it’s fun.

  21. I love when you post Sam and I literally have the conversation with my wife about this same topic what feels like moments ago.

    Some of the items that are similar include renting out the property as our tenants have informed us they will be leaving when the lease comes due in a couple months. While our strategy is not to sell today it most likely will happen next year. Our biggest dilemma is we have an older property and plan to move 2,000 miles away, while the rental income will be above average I can’t imagine not getting a few calls on fixing this and that. With time the house will need more fixing, especially one from 1912, while the age is common in Chicago I’m sure fixing and patching these homes are as well.

    We won’t walk away with nearly as much money, but since we also live in this rental the profits will be tax-free. We certainly have a 5-year window to see if we can manage a property/property manager from long distance, but I can certainly see making a move and pivoting putting that money in an alternate passive income location as you mentioned.

    The entire time we have owned this home we have essentially used it as a cash cow to pay down another rental and that milestone is on track for this year. Once we get reach the milestone, serious talks will be had about simplifying. For your situation, I would suggest holding the property for life, if we stayed in Chicago we would do the same. Based on your tone I think having someone deal with the property management/landlord details would be a better approach moving foward, simplify but don’t sell.

  22. PatientWealthBuilder

    First of all – if you really are serious about lending money at 5.5% I am interested. I am looking to buy another rental in the next two years to grow my real estate portfolio slowly and would be interested in working with you (seriously).

    Second of all – I really think the answer to your quandary is to get a property manager. Yes I see you are asking “but who manages the manager?” and I get what you are saying. Ultimately if you want to de-stress etc. you should just sell the property. No doubt you could invest the money in an index fund and probably do just as well (or better). You could also lend some to me for 5.5% with guaranteed repayment (just saying:))

    But I don’t really think it would be too bad to manage a property manager; especially on a valuable property such as yours. The front-end process of shopping for manager may take some time as you negotiate the best terms and lowest fee (I am paying 8% gross rent to mine) and so forth. I do absolutely nothing with managing my manager. All that happens is I get the money direct deposited and a statement each month. Everything else is handled. Its like magic. I am obsessed with property managers –

    My experience with property managers has been so good and my adventures at being the landlord myself have been so bad that I will never manage a property on my own again. And hopefully I’ll never have to clean up drug paraphernalia from my property again either!

    Interesting Post! thanks

  23. I’ve had this same dilemma myself with my lone rental unit. About a year ago I was really leaning towards just getting rid of the thing after having a tenant turnover and a number of repairs cut into any profits I might have seen. In my case, I don’t even hardly cash flow more than $50 bucks a month if I’m lucky. But – I decided to stick with it as good long term play. At the end of the day, the tenants still pay my mortgage, the value should rise with inflation, and I can take advantage of depreciation.

  24. Sell and deploy the cash on a multi-family outside the city with a higher cap rate. You could leverage up and buy a couple! Hire property management if you want it to be more passive!

    congrats on your decision whatever it is!

  25. Interesting post. A few thoughts, as a fellow landlord:

    -lease expiries almost always make me want to sell. Then I get the apartment rented, the headache is reduced, and I’m happy I didn’t sell.
    -to the people saying hire a property manager, just remember that you have to be happy with 80 percent. No property manager will ever take care of your property and the management the same way you will. It’s your investment, not theirs.
    -don’t focus on the one month vacancy, focus on quality tenants (sounds like you already do). Retrospectively, I have been very happy that I was picky with tenants, even though it probably means a month or two of vacancy every 1-2 years. The headache it saves at the end of the lease (and during) is well worth it.
    -if you saw your own apartment listed at 1.1 million, would you buy it at asking price? If not, lean towards selling. If so, lean towards keeping.
    -vacancy can be a great time for renovations. Look at this as forced appreciation if you renovate.
    -a 3.8 cap is crazy low. Is it sustainable? We built our units at a 13 cap minimum (secondary market). I would sell at a 6.5 cap. If you can sell at half the cap rate at which you bought, that is a massive windfall.
    -the biggest issue I struggle with is what do I do with the cash if I sell? I would probably deploy to a bigger project, which can mean a bigger headache. Be careful what you wish for.

  26. OlderAndWiser

    What would be the effect of traffic to this site if you were to sell the rental property? One of the things that makes your blog interesting is that you have so many different, interesting things going on in your financial life.

    Have you ever thought about getting your real estate license so that you no longer have to pay commissions? What would it involve in terms of cost and time? If I owned as many properties as you do, getting my RE license is something I’d be thinking about. Plus, it would give you something new to blog about.

    Looking forward to reading about the crowdsourcing real estate industry.

    1. Good, interesting question, but nothing happens actually since 74% of my traffic is from organic search, and regular readers aren’t the ones who pay the bills. It’s those with a problem who search for that problem online who are more likely to take action on my site.

      My real estate related posts live on forever. Many are evergreen, as I’ve purposefully used the strategy of telling a story and highlighting helping strategies to make a decision. This is the beauty of blogging. Once the post is out in the world, it’s like a tiny passive income engine that adds to the overall pie forever. Some posts I’ve written 5 years ago generate 50,000 pageviews a month still! And even at just 1 penny a pageview, that’s $500 every single month in passive revenue.

      And if I sell my rental, I still have two more! Endless stuff to talk about.

  27. Sam – I think you said in another post that you believe interest rates will remain low (lower?) for some time.
    Wouldn’t the current yield of your rental widen the gap with bonds in the coming years?
    If you don’t want to manage the property but want to keep the passive income, a property manager might be the way to go.
    Selling and investing in RealtyShare instead might be an alternative worth evaluating too.

    1. Yes, the yield gap should widen due to a increase in rent by 5% this year. I’m pretty sure I could do it. With the 10-year yield at 1.72% now….. I’m not sure how low it goes. Maybe 1.5%? If so, I’ll try and refinance another property and go through the pain.

      Funny you mention RealtyShares, the CFO just contacted me about working with them who came from Motif, where I do some consulting work. Small world! I’ve got an article on the crowdsourcing real estate industry soon. Stay tuned. Good insights!

  28. Nuclear Real Estate


    You have a strong recurring theme of wanting to simplify your life, and embracing freedom across many of your posts this year. I’d suggest that an option you didn’t list for what to do with the proceeds from a sale, that would be most aligned with the goal of life simplification, would be to sell the rental and pay off the mortgage on your primary. None of the hassles of being a landlord, none of the hassles of dealing with refinance requirements that defy logic, no more escrow accounts, etc.

    This is coming from someone who in two week will be closing on his 7th rental in 4 years, with the plan of buying another in August, and 11 more (19 total) by June 2019. But the property I am closing on in two weeks will have a cap rate of 13.5% (I have a tenant moving in the day after close). A cap rate of <4%, would not be worth the headache to me, as being a landlord is not just an investment, it is a side-hustle.

    Of course if you wanted to roll the proceeds into a private money loan @5.5% I'd be all for that :)

    1. I’m almost done with my mortgage refinance, thank goodness! It looks like I will pull through!

      Bless you for being about to manage 7 rentals with a goal of 19. How old are you?

      I can lend you money at 5.5% if you promise to pay me back!

      1. Nuclear Real Estate

        I am 29, been around rental properties my whole life as my dad owned/managed 14 units all while growing up and still does so for 10 of them after selling a 4-unit building 3 yrs back. What I learned from helping him, and what I do differently is that all my units are upscale, high end of the local market, so I have less headaches than he does.

        When I left the bay area and moved to Augusta, GA 4 years ago I bought 2 townhomes on the same street and lived in one and rented the other, and things have just gone from there. I’ve maintained a very low vacancy rate, but not without drama. Earlier this year I evicted a tenant who was breeding pit bulls in the property. Had $4k+ in damages, but had them out on a Sunday and had everything repaired and a new tenant in 6 days later the following Saturday at a $125/month higher rent to boot. Tenants were military so I got every cent recovered.

        It takes a certain mindset to not be emotional about any of it. It’s a business, and its all just numbers.

        I would do 5.5% private loans all day long; 80% LTV, deed of trust arrangement. The 19 goal comes from the limits of conventional financing, where you have 10 mortgages in your name. So I will have 8 next month, my primary + 7 rentals. Plan is to buy 2 more in my name, then start putting rentals in my wife’s name. Private loans at that rate would raise my target as I’d keep putting more and more in my name.

        1. Yikes about the damage and stuff. I was fine managing as a 29yo too. I do wonder if things will change 10 years from now. My attitude certainly has bc I found new revenue streams that are much more rewarding. Keep at it until you can’t take it anymore!

  29. Initially, I was going to tell you to just keep the property and find new tenants. It sounds like a great income producing investment, and I love me anything that produces income. The problem with that sort of advice is that it’s easy to tell some to man up and do the work, but not so easy to do it yourself. All we see is the numbers; only you experience the sacrifice and sweat it takes to achieve them.

    So instead, I would say sell the property and use that money to invest in dividend stocks. Not a dividend ETF as I don’t care for funds, but a swath of dividend growth stocks across multiple industries. I don’t think there exists a better passive income investment out there. None of the companies you buy will call you in the middle of the night to fix something.

    Alternatively, you can always go with hiring the property manager.

    ARB–Angry Retail Banker

  30. The Professor

    Good article. I live in Southern CA. and sold my first place I bought almost 30 years ago when I was in my late 20’s in December of last year. It was time. I had no mortgage on it and it had been a solid rental for over 6 years without missing a month. (next to a major university)
    I decided to test the market and if I didn’t get my asking price I would increase it a bit and rent it for a while longer. I netted around $230k on this condo after taxes, etc. and used it to pay down my principal residence. I’m about a month or two out from being mortgage free on my principal residence which also has an extra room I could rent out on another floor at $1,000/month if I want so income potential is there.
    I have no regrets but I’m a bit older (in my 50’s) and have an eventual pension coming also.
    Life is definitely simpler now.

  31. Sam,
    I vote to sell it and you can buy a place in Hawaii near your parents. Life is short and you always said that you want a place in Hawaii so go for it. Just keep one house in SF if you like.

    I just checked the CA munis and you can get 3-3.125% bonds around PAR if you want work free passive income.

    My parents have rentals and I can’t deal with tenants. Their 2 houses from the 70’s were 65-70K each and are worth now 900K to 1.35mil each but I am not jealous nor I feel that I lost an opportunity to make more money. Our IT jobs are stressful enough and we don’t want another job. Our net worth is all from brute forced savings. We save 85% of our income for the last 5 years. We are mortgage free for the last 14 years. We only invest in munis and only have one small house less than 1,000 Sq ft.

    Our 4-5% munis generate 85K of tax free income every year. My parents rentals don’t even generate that much money and they have the hassle of dealing with issues.

    I believe in simplify your life. Sounds like you don’t need that much passive income from rentals then why subjective yourself to unnecessary stress?

    But part of you is worried about the future value and lost opportunity. If you don’t need the money then why worry about making more money? My father spent his whole life working very hard and accumulated assets but he got 2 types of cancer and died over 10 years ago. He NEVER got to enjoy retirement. In fact, His illness retired him and he died a painful death.

    I say sell, move to Hawaii, have a couple of kids, enjoy the company of your parents/family and live a stress free life.

      1. Sam,
        I checked the Fidelity site last night for your state CA and I saw several 3-3.125% bonds around PAR.

        I brought a lot of 4% munis around PAR last Jan thru March 2015.

        The 5% muni bonds were purchased 4-6 years ago. many of them had a premium of $104-$108 and some at PAR. My YTW on average is around 4% for all of my bonds.

        These days the 5% bonds for my state are around $110 to $120 which is too expensive for me so I wait. I am very patient muni bond shopper.

  32. Midwestern Landlord

    It is a little hard to relate to the rents and values in the Bay area which certainly goes into the equation. Said that, I don’t really understand the hardship in managing a few rental units. I own and manage a lot more than that and my life is pretty leisurely. Granted you are doing other things as well that generate income for you. But I wouldn’t exactly call those activities completely passive either. So it boils down to how you want to spend your time. If managing rental real estate now puts a bad taste in your mouth, it may be time to sell. The value of the property has certainly had a nice run up since 2003.

  33. I think the real question is “do I want to be a landlord?”, which only you can answer. Otherwise, you’re asking us about market timing, which you know the answer to as well. Of course it’s a great time to realize your gains since you’ve basically seen a 40% return on your down payment every year for 13 years…plus the income you made in the meantime.

    1. I don’t think that is the right question, because nobody wants to be a landlord if they had a choice. I’ve been a landlord because I enjoyed owning the property and generating income for my retirement. But given that I have not spend a penny of my passive income since I left In 2012, the property is actually not providing any benefit, only headache.

  34. David Michael

    Great topic! I will give my insight based on the fact in six months I’ll be 80 and at age 40 I used to live and work in the Palo Alto-Los Altos area.

    1) Nearly all of my colleagues in college teaching are multimillionaires today. They bought one house for around $40,000, as I did in late 1960, made the payments, struggled from pay check to pay check, and eventually bought at least one more house as a rental in the less expensive areas of Milpitas or Mountain View. Today, they not only have an incredible teacher’s pension for life with health care, but their two houses mushroomed to 2-3 million dollars each in value.

    2) I, on the other hand, dropped out of teaching at mid-career to pursue my dream of forming a travel company. Sold our one house at $250,000 level (instead of a cool two million which was the eventual value), split the proceeds with my ex-wife as part of the divorce settlement, then moved to Oregon to live the dream. My company was moderately successful but there was only money to buy one house. I sold the company after 20 years and retired. My second wife and I then traveled for 15 years about the world and lived our second dream of “world travel.” Now, we are back home, have a small pension and live in a cozy apartment living primarily off social security…plus working part-time on a seasonal basis. The one thing I wish we had done is to buy and keep a second house that would have served as a rental as we travelled and lived our dreams. A property manger would have been a necessary part of the equation.

    At some point, dreams become fulfilled and we all return home, older and wiser. But what kind of home? Even a small condo would have been great for us, completely paid off, and making money as a rental for 10-20-30 years. So, my advice to live the dream… simplify, simplify, simplify. But…keep at least one rental as your homestead so that on your return you have a retirement home. Our one house in the Bay area went from $37,000 to $2.5 million in 30 years. Who knows what homes will be worth in another 20-30 years?

    1. This is wonderful insight. Thanks David! And happy 80th!

      “At some point, dreams become fulfilled and we all return home, older and wiser.” – love this.

      Could you have ever imagined your $37,000 home could one day be valued at $2.5M? If not, what do you think the max it would ever go to? I know inflation makes the real value appreciation not as great, but still, $2.5M is $2.5M!

      I ask myself this question all the time and also conclude in the post, “Will I be kicking myself 20 years from now if I sell today?”

      Will a $2.5M home really be worth $5M in another 20-3 years? Maybe!

      I felt strongly that the condo I bought for $580,000 would be worth $1M one day due to the view. But I’m biased.

    2. Wow, 80!
      Thank you for sharing the insights, such experience is invaluable.
      If you don’t mind, I have a few follow up questions.
      1. When you retired, what funds your travel?, Other than pension, do you have any other investment to support your retirement?
      2. Since you have traveled for 15 years around the world, have you considered to actually settle in one of lower living cost places out of US, other than SF? The dollars from the pension can go further? What’s the reason to settle in the US now?


  35. 3.8% cap rate implies extreme overvaluation IMO. Even trophy hotel properties in NYC/SF/etc that attract not only Americans but Chinese, Brazilian and Russian Billionaires as buyers go for like 5% cap rates (and industry as a whole is around 8-9%). Add in private valuations at serious risk which means less massive big pay days in the area (potentially)….Personally, I’d sell and diversify the 1 million net into 3-4 different investment options you listed and maybe a couple others as well (international fund, gold/silver ETF, etc). Out my way you could by 7-8 rental townhomes outright and get 8-10% returns and let someone else manage it (assuming 0% property inflation and 10-12% vac/maintenance combined)

    1. A 3.8% cap rate has actually been like this since I came to SF in 2001. I had the same hesitation when I bought in 2003. Yet, SF has remained resilient due to the tech boom.

      But I agree with you, if I could snap my fingers and reallocate proceeds to 8-10% returns somewhere else, I probably would to diversify.

      1. Yup its remained resilience due to the tech boom, specifically a whole lot of new millionaires, and interest from overseas buyers. Will that continue at the same pace pushing prices higher? Possibly – Given recent private valuation sketchiness and I believe a recession is imminent who knows? But you’re way, way in the money on the property.

        To me, property like that is no different than a spec stock trade that works out really well. You know there is a chance it might continue to soar higher but I find its generally best not to get too greedy on a single investment – especially one that makes up an extremely large % of your NW. Normally I’d just say at least take some money off the table with a stock trade. Maybe you could find an interested party (person or investment group) to buy half the stake so you could partially cash out.

        1. I don’t think prices will continue at this pace, no way. Prices will flatten and fall probably 10-15%, stay that way for 3-4 years, and we’ll see what happens again.

          Finding someone interested in buying a portion could be good, but that involves dealing with more people, which I’m trying to minimize.

    2. Steve Adams

      Hi Rob – where is out your way? I think real estate is well valued lots of places but have been wrong often enough to ignore what I think a little and keep looking.

  36. Financial Slacker

    Sell the property for the $1.1 million (or better). It doesn’t sound like you really want to be a landlord. It will just continue to frustrate you.

    If you’re comfortable with your income stream (combined passive and active), redeploy the proceeds into the venture debt fund.

    Otherwise, buy the 5 year CD and consider redeploying back into real estate at maturity if you find that you still want to own rental property.

    I can’t recall reading if you have a significant position in dividend stocks. If not, you could also start moving the proceeds in that direction. Although I would probably hold off for 12 to 18 months unless we see a significant market correction.

  37. A 1031 opportunity would make selling easier to do…perhaps something like a true vacation property that you can enjoy with good management in place. The taxes will outweigh any future management costs

    Also, be sure to mention that there are no capital gains if owner lived in residence for 2 of previous 5 years. Deciding whether to take advantage of this law is a big decision.

    1. Yep. I might just have to set up residency there for 2 years to get my tax liability down! But I think the law has changed to be less tax advantageous for sellers who’ve already rented out the place for a while. I have to double check.

      1. Yes the law has changed! Unfortunately it is not that easy. I’ve dealt with many expats that have rented their homes while they went on assignment and often they think they can move back in for 2 years to mitigate their tax liability. Talk to a CPA and/or look in to it.

  38. Sam,

    Good timing on this post. I go back and forth quite a bit about buying or renting out my current condo if we move to a different state.

    If you did sell, would you consider investing the proceeds in a REIT for a mixture of both simplicity and real estate exposure?

  39. Working Bee

    I was also pondering if I should sell one rental for the past few months.

    After my conversation with one of my tenants last weekend going like this —
    She said” We are not gonna pay you rent for May.”
    “So when are you paying?” “ I don’t know, we got other bills to pay”

    So she thinks I have no mortgage, no property tax, insurance bills to pay?

    So my tenants helped me the make the decision. I would sell in May or summer, and not sure if I will come back to replace another later. Most likely Not!

    1. Oh wow…. that would severely make me sad. I cannot deal with folks who do not honor their commitments. I do think renters sometimes forget the landlord has a lot of financial obligations as well!

  40. Sell and buy VNQ, the Vanguard REIT Index ETF. 4% yield. Taxable as ordinary income however.

    I have been thinking about doing the same tbh.

  41. Sell!!! That’s what I’m also doing in SF now. Timing is good, and your return on equity is not good staying in the property at 3.6% without much additional leverage… that’s too low, especially considering the short-term downside risk of SF real estate! You can certainly find better returns elsewhere.

  42. I am not familiar with US rental laws, but you could consider:

    – inserting a clause in your rental contract that inside maintenance is the responsibility of the tenant. I would never dream of responding to a call re eg a clogged toilet – it’s the tenants responsibility. If something is broken when they move out, you take the cost of the repair out of their deposit.

    – consider extending the notice period to 3 months for the next tenant. Gives you more time to prepare.

    1. My rental property lease specifies: 1. Repairs under $100 are tenant responsibility. 2. Tenant is responsible to be at the property to admit the handyman or anyone who needs to access the home for repairs, utilities, etc. Property is across the country, so I cannot be there for these issues. Digital pictures and video help me understand any issues, as does a terrific handyman I trust. This arrangement has worked well for eleven years.

      That being said, my tenants of five years are leaving. :( After looking at the positive but disappointing cash flow over the years, increasing taxes and slow appreciation, I am selling. I can make more passive income investing the cash proceeds elsewhere. Listing agreement will give the RE brokerage 45 days to reach a binding contract. If property fails to sell, I will rent it again.

  43. I didnt read all the comments but, would you ever consider using it to Air BNB? You could potentially make much more than what you do renting. However, the drawback may be a bit more work than you are looking for. Another benefit is you dont have to be up to code like rentals and you could hire a housekeeper to turn it over between guests at a fraction of the cost of a property manager. Let me know what you think.

  44. I personally would sell. Based on your numbers, and it only being a condo, this appears to be an incredibly risky investment. There is some upside potential, but equally could be a large downside risk, with very little yield.

    I love investing in residential real estate, but at some stage I will get sick of the work, and will look into NNN commercial investment. You get many of the benefits of real estate, with none of the headache, as commercial tenants manage all their own taxes / maintenance. These yield quite low, but once you have the capital are worthwhile. Seems much more preferable than what you hold.

    1. Tell me more about why you think this property has been a risky investment since 2003? If I could go back in time, I would buy two and ask my parents to give me all their money to buy more! :)

      The rough math is $120,000 down on $580k purchase, and if sold for $1.1M, the return would be $640,000 gross for a 433% return pre tax and if I didn’t pay down a single dollar of principal. But given the mortgage is paid off, after 13 years, it could be around $1M net from just $120K.

      What are some investments that have done well for you and what types of RE are you investing in?


      1. To touch on the element of risk, are you concerned about an impending wave of supply putting downward pressure on condo prices in SF? Although this is anecdotal, I’ve noticed that several large buildings have been under construction 2-3 years and it seems like the first waves will finish with a bunch more opening after.

        Maybe you could sell the condo and buy a single family home? That way you’d still be in RE, but would be exposed to more sensitive Condo price fluctuations?

  45. My personal feeling is that you should get a property manager if the concern is simply time management. However, you would need to calculate the fees of the property manager and compare THAT to the other alternative investments. That CD or Muni Bond may look comparable after manager fees.

    My gut feeling though is you’re going to bite the bullet and put in another tenant. No Wall Street banker, current or not, sells an illiquid asset in a falling market unless they need the present value of the cash flow. Considering you’re already in early-retirement, I’m guessing you don’t.

    1. I’m not exactly sure the market is falling yet, I’ve just heard the multi-offers have faded, and there are price cuts from very high asking prices. The market could be 10% lower in 2 years. If so, better to sell now.

  46. Sam, you said $1,120,000 nets you $1,000,000 after taxes and fees. Did you account for federal and state capital gains taxes correctly? Your cost basis is low, and not sure if you were in the property 2 of the last 5 years, and your marital status at the time.
    Another thing to consider is the property tax benefit you have on the property. You have a $1,120,000 property, but you are paying property taxes for only half that value (your cost basis).

    1. It’s a rough estimate to make math easier for the return on the reinvestments. LT capital gains tax rate of 20%, increased cost basis for being net negative the first couple years of renting etc.

  47. If it is available at your dollar amount (you need to be an accredited investor which you are, but unsure if 1 million is enough to have this arranged in a cost effective manner), there is a mechanism (google upreit) to combine a 1031 and 721 exchange to end up with taxes deferred and a private piece in public reits and if you wish, sell your interest in the public markets over time (converting to public makes it immediately taxable but you can do it in pieces). I do not know a great deal about this, but would have tax benefits over just selling and diversification benefits over a normal 1031 exchange.

    Even absent tax deferral, I would cash out and invest elsewhere at those cap rates (I would just choose broad based index funds but, for what I presume are saying you achieved a goal reasons, you seem set on income like DVY which is less tax efficient)

      1. Ms. Conviviality

        Another option you may want to consider is a Deferred Sales Trust which would also allow you to defer payment of capital gains tax. You would sell the property to the trust. Then the trust would sell the property. No payment of capital gains tax as long as the principal (sales proceeds) stay in the trust. The trust could be used to invest in pretty much anything (i.e. REIT’s, stocks, bonds, annuities, loans to yourself, etc.) and you would only pay income tax on the earnings. The trust could even be passed on to your heirs without you ever having to pay capital gains tax. Of course, if your heirs take out the principal then they would pay the capital gains tax.

  48. I went through this twice in the last year when the tenants moved out of the two rentals I still manage. It’s interesting that I don’t agonize about buying vs selling when my managed rentals have a vacancy. But those aren’t as desirable as owner-occupied homes either.

    I decided to hold both times mainly because I don’t know what to do with the cash I’d get from selling. I don’t want to buy more property at current prices, the stock market is also frothy, bonds are headed nowhere but down over the next decade or so, and cash is barely competing with inflation.

    Also though, one of the properties is a good backup for me if I ever want to move back into it (if my husband croaks or we divorce). In fact it doesn’t even cash flow, but because it’s on a 15 year mortgage the equity build up each month is pretty solid, plus it has appreciated nicely in the last 5 years.

    1. Yes, it’s tough to find decent investment alternatives with the proceeds. Real estate crowdsourcing investments actually did well in 2015, and is up ~6-7% YTD.

      Having at least one of the rentals sounds good.

  49. This is a really interesting dilemma (and one we are actually going to start working on this summer too – with an 8 unit place we own!) *Quick disclaimer – I am in Education, studied Decision Analysis as a conceptual framework and wrote a “Decision Making” dissertation. I am far from an expert in finance but I do own multiple rental properties so that is my “lens”…(and I also bought my first property at 25 – a foreclosure no less…and I still own it 20+ years later because of the view!)
    You started your post with subjective comments which is interesting in itself from a finance guy. It speaks a lot to what matters most to you right now. (We’d call those your “extremely important” objectives our decision-making framework.) Things like “simply my life”, “happiness and freedom” and avoiding landlord type “work” came through clear. You add “Despite the reduced income, I will enjoy not having to manage this property more than the loss.” That was a pretty powerful statement.
    What we learned in my coursework is that it is really important to spend time on that “decision problem” upfront. Often a “triggering event” (like a tenant moving out) can bias something that would never have been a decision in the first place. Is the problem really “rent or sell”? Is it “how do I generate the 200K in passive income”? Or is it something else? (I see your comments about your family/kids maybe living there someday.) This could all be complicating your decision. You have shown other ways to generate most (if not all of that income) – so I think your subjective “side” really matters here.
    I will be interested to follow these comments as I am pursuing “decision coaching” as possible future work. You might re-visit that decision problem and rank the things that “matter most” then compare the alternatives.
    Your comment “when you have total freedom, having to do things you don’t want to do feels EXTRA BAD.” I SO AGREE WITH THIS – especially today. I was reading your post during my last “department meeting” as a full-time faculty member…scaling back to part-time now as “FI” is not just a dream.

    1. Such a wonderful and insightful comment Vicki. Thank you!

      You are right about the Trigger Event that may be irrationally pushing me to sell when I didn’t plan to. But I have been writing about my negative view on real estate this year, so I’m thinking this trigger event might be destiny to test the selling waters. See:

      I’m extensively thorough bc I’ve made so many mistakes before. This is why I like to write and share my thoughts to shine light on blindspots. I recommend other folks do the same. ( Your comment is a gem that allows me to think things over further before my tenants move out end of month.

      I’ve shared my subjective thoughts and objective numbers in the post. I’m happy to share more thoughts publicly if you want to use me as a Guinea pig for your decision coaching!

  50. I like reading the votes & posts by fellow commenters! Not sure I can add much to their wisdom. My financial vote went to “hold on and see if you can get the price you want.” While a property mgmt. company might make the numbers work for a awhile, it’s not mentally restful. You’re already financially free.

    Would you be willing to park the decision for 60-90 days? Or does the thought make your blood pressure go up? Sorry, I don’t want to cause stress. This decision is where raw finance meets heart/lifestyle. I know time is money, but this one’s worth some time. Even in 3 weeks you could be in a different head-space, or something shifts in your family/community to better inform the decision.

    1. 2-3 months is $8,000 – $12,000 in lost revenue. I could do it for the ultimate tenant, but it sure would be nice to have that income, even if I won’t use it.

      I hope when I get back from Europe on 5/30, I’ll have a closer solution/idea of what to do.

  51. Maybe hire a property manager? That way you could keep the house, and have the option to sell in the future, and you would still be generating income, with less hassle.

  52. I ran into this question when I bought my new property last fall. Basically, sell my current condo or rent it out. I wasn’t going to be just breaking even on the old condo with the current rental prices in Los Angeles, but the condo was in downtown which is seeing a huge boom and I knew it wouldn’t be long before I started ticking up and up that passive income stream.

    Still, my realtor said, “Let’s just try it on the market for a month and see what we get.” I couldn’t argue with that, and was shocked when someone came in $75K over asking on the first day we showed it.

    I decided to take the money. Like you, the thought of being a landlord didn’t really excite me. I had done the work, actually managing a twenty-four unit apartment complex, a few years before and it was a lot of work. Sure, this was twenty-three units less, but I know all to well it’s always that “one,” tenant that is the pain. Most people pay on time, stay relatively to themselves, and are super easy to work with. One or two bad apples basically generate 80+% of the work.

    So, there was the fear of finding a good tenant, and not getting a problem, and also the idea of, take the $575K off the table for this condo and put it into an investment property that would not only appreciate nicely, but also generate a bit more income today. So, that’s what I’ve been doing. I’m currently looking for duplex and triplex properties, passively, in up and coming areas like Boyle Heights, Mount Washington and Eagle Rock and the money goes a LOT farther there.

    And, now I’m sort of thinking of renting my new place, since I could easily cover my monthly thanks to my recent refinance, and start generating some cash on this property instead.

    I do know my old condo is going to appreciate nicely over the next few years, but cashing out at a great price didn’t really bother me, since my new place was only a few blocks away and bigger, better and in a Mills Act building that afforded a huge tax savings. So, I don’t consider it selling an asset so much as trading up to a better one and allowing me to have some cash to invest elsewhere instead.

    1. Sounds like everything worked out! Yes, I fear not finding a good tenant even though all tenants since 2005 have been fine so far. I also fear wasting a month trying to sell the place and discovering the offers are lower than expected. Fear of the unknown like usual!

      Part of the option to hold and not rent out is to protect myself from fear of the unknown. It’s kinda interesting, and not the decision I will ultimately take. But I do believe it could be a reason.

  53. The Green Swan

    My answer was somewhere in between finding new tenants and selling if you can relative to the comps. The passive income is important for your lifestyle and goals so don’t kick yourself down the road if you get rid of a possible chunk of the passive income just to avoid the pain now. My impulsive side was tempted to suggest selling if you can get the right price. Sounds like you have fully analyzed this so the next step is to step away, re-energize, and make a decision on Monday.

  54. HappyBeingMe

    If you sell now you will have to pay 20% tax on the capital gain .
    “Step up in cost basis” is a way to avoid this. Your wife and kids will
    thank you.
    Hire a property manager or use 1031 to trade to some other real
    estate assets.

    1. Yes, good reminder on the “step up in cost basis.” 1031 exchange is definitely a thought. I have to see how long I have once I sell… I think it’s 90 days to buy a new property, but I forget.

      1. “step up in cost basis” applies to ALL properties, not just primary resident, that’s why it’s so powerful. My friend lost her husband in 2004, she did a combination of “step up” and 500K tax exception and paid 0 tax when she sold her property in 2006. Yes, you can still file as married couple up to 2 years after one spouse passes. I will try to “only 1031 (maybe to NNN commercial RE???) and never sell” and leave all my RE holdings for my spouse and kids. I am willing to pay tax on stock gains to finance my retirement. Hong Kong properties went up 12 times in the last 30 years….
        Hong Kong, SF, NYC have something in common: local officials will continue to restrict building.
        SF is such a special place, hold on and don’t let go… especially if you plan on living there forever, and if you plan on having kids and want them to live near by.
        My 80+ years old Real Estate mentor hated hiring property managers too for many years, but he recommends it now.. He said it takes time to find good ones, but there are good ones out there. The only way for you to grow bigger is to hire good help and delegate work. You have to be willing to lose some control of the little things.

  55. I was thinking about you reading an article about how tech layoff in Silicon Valley is under reported. And the start up ipo is the lowest since 2012. Time to sell? Stay ahead of the curve. Live off the cash generated from safe investment before trump or Hillary shock the market?

    1. Things have definitely slowed down. People are taking a wait and see approach. I’ve taken a more active approach and increased my savings and reduced my allocation to equities.

      1. Sam what percentage are you in equities now? My allocation is 40% SF condo, 25% cash, 30% equities and 5% bonds. Feeling overexposed to deall estate and equities here

  56. Except for a few real stinkers, I’ve regretted selling every rental I’ve sold. Finding a new tenant is a short term pain and like others have said, if you are in it for the cash flow, a sale now doesn’t really help meet that goal. Regarding tenant hassles, maybe re-framing the situation to realize that your tenants are your customers (& funding your early retirement)! Then, doing whatever you can to make them reasonably happy and keep your rentals profitable is less work and more fun. That, or hire a PM. :)

    Last, I’m not a blogger so I don’t know how secure that income is, but I’d point out that rental income has been funding retirements for many, many years – will online income be here in 50 more years? I’m not sure. So, in summary, I’d keep the rental – vote locked in!

    1. Hi Dave,

      Thanks for sharing your thoughts. The large majority of people who’ve sold a rental have told me they regretted it years later. But I don’t know how many of them found a new passion in an online business or blogging?

      I never thought FS would grow to where it is today. I was thinking maybe half the size (and revenue) five years from now. Everything is relative, and b/c I love blogging, I don’t love RE as much.

      I will rent to an awesome tenant who loves the place. That’s all I want. A person who follows the lease and is so happy to be there. It makes me happy to provide a property that makes someone else happy. I just don’t know if I can find someone, and my parents and sister don’t want to move in either. So I’m like, “if nobody loves it, and I don’t need it, why not just sell?”

      So, I’m going to see what tenants I can attract AND see what type of price I could get in a pocket listing. I that’s a nice dual strategy.

      1. Thanks for the thoughtful reply, Sam. I think that you’ve definitely thought this through and have made a best decision for you based on the facts at this time… that’s really the best any of can really do! I hope it works, and really, I don’t think either way (sell or rent) is going to be a wrong choice.

        One extra note: this statement and the similar one I wrote, “The large majority of people who’ve sold a rental have told me they regretted it years later.” really doesn’t take into account that events always look more rosy when looking at the past, so all of us ‘regretful sellers’ may just be overlooking all the headaches and hassles we WOULD have had if we had kept those rentals. Food for thought! :) Good luck!!

  57. Other:

    Can you outsource the property management reliably? I know my real estate agent here in the East Bay has people in her firm and contacts she trusts to recommend for property management.

    I think around here it is often about ~5% of rent with invoicing for maintenance (tax deductible stuff at any rate, and now you get YOUR time back not fixing sinks and the like). So you would have some loss, but not too much.

    The management fee in of itself appears to be a tax deduction. My quick research is not panning out as firm an answer as I would like, but it does show up )

    We are flipping my original property this summer, that has been a rental, on the last year I am eligible for the capital gains exemption. I feel that with the softness trickling down from the high end AND the dubiousness of an election year it is a good time to do this. Also, we get the double dip on this in that I get to minimize my economic leak and reduce my headache!

  58. Mr. Tako @ Mr. Tako Escapes

    Owning physical property is always a hassle. There’s always something to fix, or some fee increase or other.

    I prefer to use REITs for my real estate investment. They’re not quite the same, but I’ve done pretty well by them.

  59. Todd Guthrie

    You could always let your friends or loved ones live in the property for free, or for a big discount. You do seem to get a lot of joy out of helping the people you care about.

    If you were to ever have a kid, then you could keep that place for them to live in when they go off to college, so they can live an independent lifestyle without the financial burden of paying high city rents. Unlike what seems to be the case with your obnoxious neighbors, I do believe it is possible to give an adult child financial help without spoiling them.

    Another thing: if you don’t like personally managing property, you could hire a management company to do it all for you. Not sure if it’d be better or worse than your Tahoe third-party management experience.

    Anyway, I think you’d be crazy to sell any San Francisco real estate if you don’t have to. But if lifestyle simplicity is what you’re looking for, them you can’t get much simpler than cash in the bank.

    1. Todd,

      You are right. And I did ask my mom and dad whether they wanted to move to SF from Honolulu, be closer to me and live in the condo for free. I would LOVE for my parents to live closer to me. So many synergies and I could be there to take care of them if they were to ever get ill or have an accident. I could take them out to eat all the amazing food here. We could go to shows and ball games. It would be amazing. Truly amazing.

      Alas, they declined my offer and I am a little sad when I think about what fun it would be to have them nearby. It would be fun to hang out in the condo where I spent two years of my life. It would be so enjoyable to have a weekly family dinner there.

      My sister is stuck in NYC for 5 more years I believe. So she can’t.

      I want this place to be there for my parents or in-laws. And maybe even my children one day if they aren’t ungrateful. I would happily forgot the $4,000 a month in rent for my family members to stay.

      Maybe I will just keep the place empty to simplify life and pay the $12,000+ a year carrying costs until I can change someone’s mind…….. :/


      1. You have just answered your question. Next, keep the Condo and hire a qualified property manager to take care of all of your Bay area properties. Simplify your daily life without having to compromise much of your passive income. Sometimes, property managers are able to get a better deal on the rental income.

  60. Sam, I go through the same thing every time tenants leave my SF condo. Maybe easier to keep mine long term, since it’s the only piece of real estate I own, a decent portion of my total income, and my back up home in case I ever want to move back to the Bay Area. In your case, since you still have the Diamond Heights home, another SF condo rental and the Tahoe place, selling this condo might make some some sense, especially to reduce your exposure to the Bay Area. Why not put it on the market for a month and see what happens? You might miss a month or two of rental income and perhaps you get a really good offer which will more than make up for that lost income. Check Zillow, they have a table that predicts the best months to sell your place and I think it’s right around the corner ;) I agree it’s hard to let go of SF real estate with so much growth going on and, like Mark F. says, the cap rates being so low. Good problems my friend.

    1. Hi Mark, I think that is a prudent strategy. It sucks to lose one month worth of income and have to spend $6000 to stage the place, but it may be worth it. I really dislike dealing with the homeowners association. Maybe this is why im more up to selling this property.

  61. DIY Money Guy

    Here is a quick and easy way that has helped me make a couple real estate decisions. Ask yourself, “Would I buy this house (again) to be a rental if I didn’t already own it?” If yes, then find new tenants and keep the rental income flowing. If not, time to sell and make you money work for you elsewhere.

    I am currently in a similar situation. My wife and I currently have a rental house with tenants that are still contemplating not renewing their lease this summer. So we need to decide to sell or find new tenants. The house was my wife’s before we married. We are approaching this decision with the same question mentioned above and the answer is “No”. So we will likely be selling. But we will be staying in the rental business since I can manage most home repairs myself and we have been spoiled with great tenants so far.

    Hope this helps! Good luck with your decision. Either way you are going to be making money. :)

    1. Wonderful question to ask.

      My answer is yes. It is so rare to get a 2/2 property with parking in Pac heights along the park with a park view! I would buy it for $1.1M, the cut off point where I would consider selling if I already did not have property. I’m just not the same person as I was in my 20s and 30s anymore. Real estate is no longer my “hope” for a freer and better life. I am already free.

      It is really interesting how quickly we adapt to our lifestyles as we change.

    2. That is very insightful in my opinion. It is exactly the question to ask and I did that in a situation with a rental condo we have owned for 6 years. Our answer is “no” so we are selling. Rent increases are bounded by the market and unit characteristics, it needs a major refresh to get more, and sale values are very high by any standard and norm. I would definitely not buy it if the situation presented itself today.

  62. If you plan to stay in the area where your rentals are, then keep the properties while real estate values fluctuate. I assumed a 15% annual vacancy rate in my rental income calculations. Also, go to Landlord dot com and screen your tenants’ credit history. The combo of excellent past landlord references plus excellent credit history (nothing over 60 days and no serial late payments over 5 years) produces excellent tenants. Takes longer to find good tenants…thus the higher vacancy rate.

    To reduce the rental hassle factor, look for tenants that are handy and capable of making or scheduling routine maintenance and repairs. Be willing to knock a few bucks off rent if they are capable of replacing the faucet gasket, painting the baseboard, or being home when the fridge is replaced.

  63. Mark Ferguson

    Why not use a property manager? After my 7 rental I started outsourcing all the management and it was well worth it. No more hassles.

    The CAP rate in SAN Fran is so low. That is crazy to me. In Colorado prices have been going bonkers and I am selling some of my rentals. But, I am going to reinvest that money in more real estate in another area.

    I also love the passive income of the internet.

    1. Steve Adams

      Yeah that’s a tough cap rate. I recently bought a small duplex a couple states away to push my education in RE a little. I started with the intent of hiring someone I knew to manage it but then quickly adjusted to my backup a local property manager firm. It was a great learning experience. Just got my monthly statement today – no issues last month at all. In my case they are earning 10% of rent and 50% every time they fill it.

      It might be worth trying a property manager for a year. If you can make it work it is great. If it fails it will make for good posts. :) Eitherway you will have some new valuable experience without lots of pain of direct tenet management. Just a thought.

      Thanks for the constant posts – lots of great stuff here.

    2. Alex Goumilevski

      Good to see you on here. I am surprised you are starting to sell some of your rentals! I thought the goal was 100 :)
      When I run numbers on my own rentals, I always include a percentage for vacancy, even if the properties are fully occupied. I typically use 6-8% of rents as a vacancy factor, since no place always stays occupied. Even of it does, you have some downtime for cleanup, etc between tenants.
      If you end up getting full occupancy, then the extra money is a bonus. If you don’t, then you’ve already accounted for it.
      However, 3-4% cap is pretty low, hard to make sustained cash long term as a business with those returns. Perhaps consider real estate outside the area after the next correction? I know many parts of the country have 10+ caps if you look in the right locations.

      Good luck and I am curious to see what you decide!


  64. You can always get a property manager and keep the place. My houses are 1,000 miles from where I live.

    Yes, it’s an expense, but it would allow you to keep most of the income and eliminate the hassle.

    So I’d keep the house. I would never think of selling in a declining market. Now’s the time to BUY!!!

    I’d consider making a couple (or few) new ebooks. In particular, write a book on starting a blog. Or write posts on it with affiliate links. Looks like to me that top sites are making a fortune on Bluehost affiliate fees and you could likely do the same.

    I’m nervous about Prosper and LC as well, but holding in place for now. We’ll see how things shake out. As long as it’s only a portion of your money is there, I don’t think it’s that big of a risk.

    1. Ten Bucks a Week

      Are you saying that now is a declining market? I’m waiting to buy when the decline happens.

      LendingClub is a concern, I’m sticking in there, I don’t think their ship will sink on this news. I’m moving my taxable funds out and keeping Roth in. I know FS doesn’t like Roth.

    2. +1 for a property manager. You lose some income, but if you believe the government will continue to prop up the markets, and continue to prop up home values, you can keep the capital appreciation, or at least punt the problem until the markets firm up.

      1. I agree with this line of comments. There is an option is to sell and 1031 into a different part of the country where you can get a better cap rate. I see lots of real estate / cap rates in my career and 3.8% is pretty weak, but I know there are lots of other considerations like transaction costs and the long-term sustainability of SF real estate. Just a thought.

    3. Agree on getting a property manager. There will be some expenses but it will make it easier for you. You can also write off the property manager’s expenses. Interesting that you think the property value in SF will continue to climb by a modest amount. Maybe it makes sense to keep the property for another year or so and sell it later.

    4. Who manages the property manager though?

      You allude to something that I haven’t been able to properly share, and that is, my online business is much more significant and much more fun to run than real estate. Stay tuned for a new post!

  65. Finding new tenants would be the way to go because passive income is your whole basis of your Financial Freedom philosophy. Stick to your guns. I’m sure that you can find people to rent it within a month. Is the demand for rentals still high in SF?

    Of course, if you get offered something north of $1.75 million then you will have to at least reconsider.

    1. I’m frankly waiting for destiny, because what are the chances that my tenants give me a 30 day notice before my 2.5 week trip, making me powerless to find a proper tenant the following month?

      I’ve noticed that if I really care about trying to keep my tenancy vacancy track record at zero, I get stressed out about this timing/fate. But if I settle for selling or just keeping the property vacant, my stress level goes way down .

      I’ll make you a deal and sell you my property for $1.35 million, a full $400,000 off your number! You can Paypal me the funds.


          1. lol. i have always wanted a 300 sq foot bedroom in silicon valley (assuming i get the bedroom that is).

            i’m just playing around for the record… im sure SF is an awesome city, but hearing about these housing prices is just laughable… 1000 sq feet condo for over 1MM ??? wow… supply and demand I guess…

          2. i’m in a smallish (midsize?) city on the east coast. avg house prices out here directly in the city for a place that size would probably be in the 250k range, maybe less considering 1000 sq feet is not really a giant dwelling. i am living in the suburbs of this city, in an apartment, which is 650-700 sq feet and i am paying in the 850-900 range per month. the quality of the part of the city i am in i would rate a 7/10. and i don’t live in a new / “luxury” apartment; it isn’t a bad area though, which is important to me. Just to throw it all in perspective.

            incomes here are much lower than SF though. a 120k income in SF seems like it would be hardly above middle class. here, avg salaried income would probably be half that. 120k here would be upper middle class and 3-4k a month would get you a nice 4000 sq foot house in the suburbs. an 80k passive income would be more than enough to live comfortably.

            i haven’t really visited large cities outside the US, but i have visited a few of the larger cities here (NY, LA, SF (once)). these places are definitely nice and “lively”. they are more expensive though… like i said, it comes back to supply and demand i guess… maybe one day i will end up in a place like that but right now i lack confidence and am somewhat of a “stuck in my ways” type of person, looking at myself in retrospect.

      1. I got a nice Nigerian guy contact me 2 days ago with some inheritance that awaits me. As soon as I get it, will be in touch, maybe I’ll invest in some US based real estate :D

        Kidding aside, I wouldn’t stress about vacancy track records and stuff like this.

        Just enjoy your vacay and that’s it. I’m sure you’re not losing money that would endanger your family (financially speaking), so it’s just some money.

        We’re currently renovating a shack we purchased at a nearby village and we’ll probably move there in about 20 years from now. Both our city apartments will be rented, we have absolutely no intention of selling anything.

        So, as someone who’s pretty conservative with all of this: rent and pay a property manager, if you dislike the work.

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