Create Win-Win Scenarios To Never Lose: A Decision To Rent Or Sell Is Made!

You'll never lose if both outcomes are a win - rent or sell

Do you have the dilemma to rent or sell your home? It's tough given the housing market is so strong now. At the same time, rent is going up as well.

I like to leave things to fate. Believing in fate helps alleviate some stress from the unknown. When my tenants gave me their 30-day notice two weeks before I was to leave on a 15-day business trip to Europe, I initially cursed the heavens. After three years of renting, why did they have to choose the month I'd be away? Damn it!

With no leasing manager, finding new tenants while abroad would be difficult because I wouldn't be able to show the place. Thus, I created a game plan that would let fate decide whether to sell the property or to continue renting it out.

Rent Or Sell? Create Winning Scenarios

The first thing I did was review Financial Samurai reader Vicki's decision matrix. Then I filled in the matrix with my own words. Reading about how to do something is useless if you don't do it yourself!

Financial Samurai Decision Matrix - rent or sell

I first filled out my thoughts going from “Simplify Life” to “Generate $36K+”. Then I zeroed in on Happiness as my number one objective. Everybody knows Financial Samurai is secretly a blog about happiness and not money right? After that, I reviewed each block and added some additional thoughts to gain a more complete picture.

Here are some takeaways from the rent or sell exercise:

1) The idea of having a property manager sounds good, but knowing me, unless the property manager was the most attentive, caring, and responsive property manager on Earth, at some point I would probably get annoyed. This is because I live in San Francisco and can do all the work myself. Next, I've rented this property out for 11 years to five different sets of tenants and during this time, there's never been one month of vacancy. I don't want to turn into a micromanager!

2) Being a landlord really isn't that bad once you've found the right tenants. The key is to find responsible tenants who pay on time, respect the neighbors, and don't cause damage. I looked back at all my previous tenants and they were all great. They all just moved out too soon for my liking (2-3 years on average). I usually went ~ 6 months before hearing from a tenant about something. Every month rent payment was paid automatically to my checking account. Landlords are spoiled when they complain about the need to find new tenants because 95% of the time landlords don't do any work!

3) Freedom is great, but because I don't have a day job, I often have excess free time and sometimes get bored. I could easily allocate some of this free time to managing the property. What's the big deal spending ~12 hours a year doing so compared with the 2,000+ hours a regular 9-to-5er puts in? I've discovered I'm getting soft in early retirement. I've reminded myself income from real estate is not passive. It's semi-passive. Besides, owning this property gives me a lot of new writing material about landlording, prospective tenants, negotiation strategy, and local economics.

Related: Ranking The Best Passive Income Streams

Setting Up The Win-Win Scenario With Rent Or Sell

One thing you may notice under the “Sell” column is there is no joy talk of receiving a ~$1,000,000 check for selling this condo which I bought for $580,500 back in 2003. I've just noticed this myself, but don't want to make any changes because I think the omission of the windfall is telling.

I view receiving a large lump sum to be a risk and a pain in the ass. The risk comes from the possibility of blowing the money on stupid stuff like a $200,000 Bentley Continental GT. The risk also comes from the possibility of reinvesting the proceeds and losing money.

I've lost money in other investments plenty of times, which is why investing with a low-cost digital wealth manager is probably the best way to go for most people. Therefore, the larger the windfall, the more I worry. I think this type of thinking is 100% contrary to the jubilation most people might feel receiving a seven figure check.

For the millionth time: more money, more problems.

Here are two good scenarios I created to come to a decision:

1) Rent out my property if I can get a new tenant for $4,100 a month or more. The previous rent was $3,995.

2) Sell my property if I can get $1,065,000 or more. I've got $65,000 in there to help pay commissions and transfer taxes to clear $1,000,000 before taxes.

I would handle finding new tenants and my real estate friend would handle the pocket listing. A pocket listing is where a property is for sale that is not listed on the Multiple Listing Service real estate agents use to publicly market the property.

I gave my real estate friend full disclosure about my decision scenario, and he agreed to a 30 day listing agreement. After all, I had 30 days before my tenants moved out, so nothing could happen before then. The rent or sell decision was difficult.

The Race Is On On Whether To Rent Or Sell

In The Red Corner: Financial Samurai

To give my agent a chance, and to test the rental waters, I started my rental listing at $4,395, 10% higher than my previous rental price. For seven days, I had some showings, but no offers. Then I dropped my price to $4,295 for one week, had additional showings, but still no offers. Finally, as I was about to leave for Europe for 15 days, I recorded a video of the place, sent prospective renters the video while I was away and told them I could show the place when I returned. Still no offers. Being away really screwed my efforts.

When I dropped my price to $4,195, I noticed a small uptick in interest, but nothing meaningful. Several mid-20 year old techie dudes visited, but they seemed to prefer only the newest amenity buildings. Trust me, everybody looks the same and comes from the same background in tech.

After six days at $4,195, I began to wonder whether I had really cocked things up because my existing tenants were finally out. Remember, I've never had a month of vacancy in my 11 years as a landlord for this property. To get a large step up in interest, I seriously considered dropping the price to $3,999 because I knew that many people in San Francisco have a $4,000 cut off for renting a two bedroom apartment or $2,000 cut off per room. Still, I held strong at $4,195.

In The Blue Corner: Real Estate Agent

Meanwhile, my real estate agent got a professional photographer to take some wonderful pictures of my place (which I used for my rental property ads). He absorbed the cost in exchange for making a potential 5% commission on my place. For some reason it took him a week to get the pictures back and throw up a website of my property. It should have only taken him one day if he was on the ball. He then proceeded to blast out the listing to his network. We decided on $1.2M.

After a week went by with no showings, we dropped the price to $1.15M. $1.2M really is a stretch price for my property that might be achievable if it was properly staged, painted, and put on MLS for the world to see. However, at this stage I wasn't interested in spending ~$7,000 for staging, $2,200 for painting, and maybe $10,000 to do a light renovation of the kitchen and one bathroom. I'd rather keep the $20,000 for myself.

Once the new blast e-mail went out announcing the new $1.15M price, we had about six showings over the course of two weeks. Remember, I'm willing to sell the condo for $1,065,000. One of the showings was a second showing for a ~50 single woman who loved the park view and location. She was totally willing to remodel the place and even considered converting it to a large one bedroom. Not smart, but her choice. There was hope for a good offer!

Perhaps it was because I didn't convey a strong desire to sell the place, my agent was lukewarm to the task. For Memorial Day weekend, he said he couldn't show the place because he was going to the Indianapolis 500. I thought about asking him to logically arrange for someone else to show the place, but instead told him, “Have fun!” I wanted to beat him!

The Winner Is Announced

Demand from renters really started heating up for some reason by the first weekend in June. Prior to this, all indicators pointed to a softening rental market due to a large supply of luxury condos hitting the market. To be fair to my real estate agent, I kept him abreast of the rental interest I was seeing, and asked him to circle back to buyers who did show interest earlier when my demand started ramping.

A couple days later, I told him I was in rental discussions with potentially awesome tenants who would commit at $4,195. They made roughly $180,000 a year and really seemed to love the place. For tenants in a competitive rental market, showing joy in the property really makes a difference to the owner.

My agent texted me, “That's awesome! But wait! How about we put your listing on the Coming Soon feature the MLS listing has? It's great because it gives your property maximum exposure and the Days On Market counter doesn't start counting until you switch categories to a full listing?

Could be good!” I responded. “But it's been 27 days, and I think destiny has called. I've got the ideal couple who will probably stay for 2-4 years. At $4,195 a month, that's $200 a month more than what I was charging, and $50,360 a year in rent. It's a bird in the hand, baby!

Related: Example Of An Excellent Rental Lease Agreement

I Always Knew What I Wanted

The deposit check is in hand

In my heart of hearts, I've always known I wanted to keep the property. You just don't always get what you want. Paying $50,000+ in commissions and another $10,000 in estimated transfer taxes along with another $100,000 in taxes on long term profits seems like a real big waste of money. Therefore, the rent or sell dilemma was tough.

Inflation is too powerful a force to combat. There's nothing easier than being long property to ride the inflation monster into the sunset. I was just bummed for having to do work to find new tenants after three years of autopilot.

I don't care about huge windfalls or making a higher return. It's about cash flow and allocating this portion of my net worth in as simple and forgettable manner possible.

It brings me happiness to see a young couple's eyes light up when they first walk into my property. They start talking about their potentially wonderful future together. And if they like the property enough to fill out an application, that means they see value in the price I'm asking.

When you create a financial plan with two good outcomes, there's no way you can lose. Even if I didn't find a buyer or a renter, I could just keep the property empty like an overseas investor looking to park his illicit cash. By removing my property from the sale or rental market, I'm also helping other landlords and property sellers find their best price due to less competition.

I strongly believe everybody should hold onto their real estate assets for as long as possible. Think about how little work is actually required to maintain an asset that can take care of your retirement years.

Related: Why I Sold My Rental Property


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Rent Or Sell Is A FS original post

About The Author

45 thoughts on “Create Win-Win Scenarios To Never Lose: A Decision To Rent Or Sell Is Made!”

  1. I’ve loved following this story and find it so creative the race you created to let fate decide on Rent vs Sell (you don’t have any copyrights on that do you :)? Glad fate /luck worked out for you, though from reading some of your other posts, I think this is due to your hard work – great job!

  2. Sounds like you made the right choice Sam!!

    I wonder if I could ever win from putting some of my assets in real estate today, especially here in Calgary (though we’re not as bad as Vancouver or Toronto). People who bought in 2003 will probably make a mint off real estate. But I’m not convinced I would if I got into real estate now.

  3. Help! May I digress and ask for some advice? I’ve been following this forum, am anxious, and thinking of selling my SFR NOW so I hold cash ready for the next buy cycle for investment properties (per the samurai it’s the winter of 2017/2018). I’ll make my situation concise:

    Will retire/stop working after selling
    Bought last April at $840k, no loan
    Put in $30k of material and did all labor myself
    Based on 2 months’ comps it’ll fetch $1m


  4. Sam, good for you. I like your decision model very much. Very good way to decide. Try out both ways at the same time.

    Great tenants make all the difference. I have been renting suites and houses for many years and have always had good tenants. Very lucky but also very picky. Renting is always a hassle because you have to prepare and show and decide. And often it is just when you are leaving town. I mentioned to your original post that I left my coach house empty for 2 months last year as I was travelling and did not want to leave it just up to my property manager. I always like to meet my tenants face to face and make that positive link when it’s right on my property where I am living. It was worth losing 2 months rent for peace of mind. Timing seems to be crucial when renting although there are no definite patterns — sometimes hardly anybody calls, and then suddenly people start to call, not the rental amount, just chance re the number of people looking in any particular month.

    Nice too that you have a great profit on the condo, but no point in paying all that tax before you have to.

    1. Thanks Dunny. Yeah, it just kind of kills me to have to pay taxes. Taxes is a great incentive to never sell! Also there are transfer tax fees as well. And then of course the 5% commission which hasn’t changed in forever, despite the invention of the internet.

      I’m glad you were able to rest east for 2 months on that rental. I’m resting easy now for one month as new tenants move in mid-July. I have absolutely no stress and qualms now. Mortgage is paid off, and I’m happy to have found tenants who will pay $4,200 and who will hopefully live there for at least 2 years.

  5. I continually evaluate the rent vs. sell scenario on a property of similar valuation but with the low interest rate, high leverage, appreciation and tax consequences, it’s a no brainer to hold on. I “engineered” a vacancy so that I could increase the rent from $3700 to $4500.

    You definitely made the right choice, but I find it difficult to believe that you of all people leave much of anything to fate ;-).

    1. Hi David – Who knows whether I really made the right choice as my new tenants could turn out to be a nightmare. BUT, I have faith my CIA-level interviewing and background check skills will pull me through. I’ve spent years honing this rental lease agreement any other landlord is free to use to protect myself from bad tenants.

      I really am a fate type of guy. Work your hardest, hope for the best, but go with what fate decided in the end :)

  6. I am so glad that there was no bad outcome, and you got what your heart truly desired. So important to know yourself.

  7. I think you made the right decision. I remember when you first brought the idea to everybody; I commented in that post that the best route to go was to find new tenants. Nothing like a good passive income stream.

    And you are right about how crazy SF real estate is! It would take about three months at my job (where I routinely work more than forty hours a week) to afford one month’s rent in your property. That’s not a knock against you; just a commentary about outrageous real estate prices.

    Congrats on finding a new tenant! And for keeping that passive income stream flowing!

    ARB–Angry Retail Banker

    1. Thanks. Yes, rent is expensive, but it also cost a lot for me to buy the property as well.

      Don’t beat yourself up. It’s a couple renting the place. So take you X 2 and you can afford it no problem! :)

      1. Me X 3.

        Real estate seems to be outrageous everywhere. In my city, regular sized houses with small amounts of land are going for over a million.

        My friends and I are looking to buy a mixed use property and rent out the storefront. It’s the only way we can afford home ownership. It’s the only way we can afford ANYTHING. Rent is unaffordable, with landlords charging over a thousand for a tiny closet in a shoddy neighborhood. But with the prices of even the smallest mixed use properties, it would be years before we can afford the down payments and closing costs. I’m hoping we can get an FHA loan; it’s our only shot.

        ARB–Angry Retail Banker

  8. Financial Slacker

    Congratulations on your new tenants!

    Sounds like you have a similar tendency to me – that is, I like to buy, but I don’t like to sell. I ran mergers & acquisitions for years, but when the time came to start selling off businesses, I left the company.

    For me, a part of selling is always feeling like I could get more. And that makes it hard to enjoy.

    Also, since I started reading your site, I now look at cash flow and think how much in investment assets would be required to generate that cash flow. So when it comes to receiving the proceeds from a sale, what can you do (in this environment) to earn something comparable to your rental? Not much.

    Thanks for sharing your thought process.

  9. Sam can you speak at all to the dilemma of trying to find tenants yourself vs. paying an agent one month’s rent to do so? I own a condo in a Washington DC suburb. Tenant of almost 4 years is moving out. I currently live in the northeast so making the back and forth treck to DC is a huge hassle. I’m back and forth about posting it myself and trying to manage it vs. paying a real estate agency one month’s rent to find me a tenant. I can’t get over spending a full month’s cash out of pocket, simply to find a tenant. Am I misguided though?

    1. Being out of state makes paying the one month rent more “worth it.” There may be a difference between a leasing agent and a management service, so best to clarify.

      If I had to leave SF, or wanted to move back to Hawaii, I would definitely pay someone to find me tenants, unless I decided to vacation in SF for a month while finding a tenant. Once you get a tenant locked in, it’s pretty auto pilot.

  10. Hi, I’m looking for an answer to this question: How much of your assets should be in your house? Age 50. Say I’m at $1 million in assets since that was the above story. I sold all my rental properties (4) because of challenges with tenants and HOA, lawsuit etc. I live in Broward County Florida. What is a good percentage in my home, pay cash no mortgage or rent and wait for the next bubble to burst? I’m curious if you have an answer..

  11. I really like how you setup the race vs. the realtor and congrats on keeping the property. If you don’t need the cash now, it’s hard to imagine a realistic scenario where holding onto the property long-term would be a bad idea.

    Also, I really like the new website design. Looks more contemporary and I think it will be more “sticky” for first time visitors. It looks really nice on a mobile phone as well (iphone) – well done!

  12. Robert Paulson

    Whenever I’m just before making some important financial decision I’m trying to look on the problem from different perspectives. That’s already allowed me to save quite a big amount of cash. Anyway thanks for your article it was quite good read actually.

  13. I am glad to read that you kept the rental, Sam. I sensed that this was your preferred outcome.

    Once again, you get to relish in the satisfaction of engineering your own deal. As you said, Financial Samurai is really a blog about happiness, and anyone who has been around for a while should realize that you find happiness in exactly these types of accomplishments. The fact that you included a picture of the deposit check in hand is indicative of just how much happiness this while process provided you.

    With your mortgage refinanced, a landlord in place, and a new design to your website, you’re going to need a new challenge. Maybe it will be time to start your travel blog?

  14. The two fantastic things I took away was 1. the money wasn’t really a motivation for you, that is just so telling for where you are in life. 2. Creating a game matrix in your head. This is something I have done for a long time, but wasn’t fully sure why until I took a course in game theory in college. At its core it’s simply an expected value assessment and incredibly useful for most decisions. Congrats on finding your way though.

    Also, the new layout on the home page: I can see it’s practicality. I definitely think it’s going to increase your page views and decrease your bounce rate, but I think it looks very busy and cluttered. I’m actually in the process of getting a new redesign for my site as well as soon as I can get a logo done.

    1. Thanks for the feedback on the homepage redesign. I think it will take time for many regular readers to get used to. But I think a lot of regular readers already signed up for my RSS or email feed, therefore, they just get the full article sent straight to them.

      How long have you had your current design? Mine was about three years, and the previous design was about four years. I’m trying to maximize the valuable real estate I’ve got. Feel free to share other criticisms and ways to improve. Everything from font size two colors to positioning and so forth. Also, check out the site on mobile and let me know your thoughts. It should seem less cluttered on mobile where 40% of the traffic comes from.

      I do care about optimizing my finances with every decision I make. The problem I think most people fine as they grow their wealth is that they become inundated with more and more options. As a result, making optimal decisions becomes more difficult. Sometimes it’s just much easier to have no options and just keep on doing the best you can with what you’ve got.

      1. I personally only view your site on desktop. I read a lot of things on mobile, mainly news articles; however, I find blogs to be irritating to read on such a tiny screen. You are right though, just with every Facebook update, people go crazy and nasty, and then everyone adapts.

        I’m actually now thinking I may wait until I get some more cash flow before a redesign. I just got Adsense and I’m starting to get some small affiliate marketing as well. Rather than spend my own money, I may hold off until my site can pay for it. The logo and avatar are still a must though, and should be up soon. I’m using a friend who is doing it for free, so it’s taking longer than I want, but beggars can’t be choosers. I’m just grateful it’s getting done.

        I can understand your pain though. While I’m not there, I do some consultations with people way above my income level. It’s kinda funny. The most wealthy of them (some upwards of $30mn) actually hate money. They have so much of it, and have the same decisions you face on a larger scale, that they’ve grown to despise it. Probably why they allow a 27 year old friend to help them out for a small fee.

  15. Todd Guthrie

    “…might be achievable if it was properly staged, painted, and put on MLS for the world to see. However, at this stage I wasn’t interested…”

    Sounds like you subconsciously sabotaged the selling effort. That should tell you it wasn’t what you really wanted anyway.

    1. Not really. Forking out $20,000 is a lot of money when I’m 50/50 on selling or deciding to rent. If the number was like $1,000, I’d do it, but $20,000 is a huge commitment that probably wouldn’t raise the rent by more than $100-$200/month.

  16. Sam,
    If you have multiple interested parties can you do a post on how do you select the finalist? Criteria for selection would be useful. Also do you do credit check for each applicant and then pick the finalist or just use the information in the application, select the finalist and then do the credit check on only the finalist?

  17. Physician On FIRE

    If you had been able to be present during this red versus blue competition, you could have gone with FSBO as an option to avoid coughing up $50k or more in realtor commissions. I have bought and sold FSBO, but I don’t know how easy or realistic it is in San Francisco.

    Just seeing numbers like that makes me wonder why I toil away when a realtor could make my salary by sellling a handful of nice properties in an expensive city. There was a realtor in NYC featured in Esquire’s 4 Women with 4 Very Different Incomes who makes $1 million per year.

  18. Always a good idea to explore all your options.

    Personally, I’d want to keep the cash flow. You can always sell when you have a need to the lump sum that isn’t an outrageously expensive car…

  19. Hi Sam, I think you made the right choice (especially since you have time to manage the property too).

    But for people who have a full-time job and are renting out a property, do you think it’s worth paying a management company to do the work? Sure the profit would be less, but it would make the income even more passive in nature too right?

    1. It depends on where you are in life. I firmly believe I don’t spend more than an hour a month on average managing my properties over the past 11 years, and I don’t believe most managers do either over the long term. If you have no other side hustle, then one should view their rental property as the side hustle for financial freedom. This is how I viewed this property. If all else failed: my job, no other investments, my business etc… I knew I’d at least have a $3,000+ a month cash flow to live.

      If I was out of state, I’d more readily consider a property manager. But when I live 3.2 miles away, no way. I’d feel like I was taking the elevator to go one floor up instead of the stairs!

      1. Nuclear Real Estate

        I echo Sam’s thoughts. Being a landlord is so much easier now than it was 10 years ago. Between online listings, esignature leases, online payment, etc. I’d say I spend less than an hour each month managing my 7 properties.

        Looking at 3 more this evening, trying to expand beyond buying my own properties, and into buying properties through LLC in which I partner with a cash member to bring all initial cash to the table while I bring all services. Should be fun!

  20. Congrats. I believe you made the right choice too.

    My property manager recently asked me if I wanted to sell my properties, so I asked him for estimated sales prices. He’s working on those now.

    I don’t want to sell but am curious about the value of my places now.

    1. Thanks. Yeah, might as well gather some info to make an informed decision. There’s a price for everything right? If someone wanted to pay me $1.2M cash for my place, I definitely would have sold. You never know until you try! It’s nice to put the pressure on.

  21. Jack Catchem

    Love the post, but it feels like you made your own luck like Thomas Edison instead of letting fate decide. Your energetic follow up and activity generated the opportunity of new renters. I often run across people at work who say fate caused an incident. I tend to look at it from a more historical viewpoint. Previous behaviors and activity mixed with an opportunity caused the outcome.

    In your positive circumcistance, your detailed market analysis and tracking led to the capture of new renters just as for some of my past customers, a history of drug use mixed with poor driving ability led to an opportunity for their arrest.

    I feel like “fate” is an oversimplification in this case. Although a credit to your humility, it undercuts the work put in!

    (Also I love the new website design. Looking good!)

    1. Appreciate your thoughts Jack. It’s nice to set up the framework where the outcomes are acceptable. Maybe that’s the general strategy in life? Work hard to find as many options as possible. Take the two best options and pit them together.

      I’ve still got like 10 more things to add to the site redesign. Hopefully all will be done by mid-week! Been putting this redesign off for 6 months already.

  22. Congrats on finding tenants and feeling good about your decision! There are a lot of moving parts with rental properties and having good tenants make such a big difference. I hope things go smoothly and that they’ll be low maintenance and self sufficient. I like how you filled out that decision matrix. It’s a great way to analyze different scenarios and hone in on your gut instincts. Side note – I love your homepage redesign! It looks sweet!!

  23. Fiscally Free

    Congrats on the new renters.
    I like letting fate work its magic. When I was looking for an old motorcycle to refurbish, I didn’t really have a preference for what I got, so I wasn’t searching hard for anything in particular. I figured I would get a bike if I happened to come across one.
    A couple months later I was on a walk and stumbled upon an old BMW motorcycle under a tattered tarp with a for sale sign. I took it as a sign and bought the bike. Now I just need to finish rebuilding it.

  24. That’s a great plan pitting yourself against your realtor. I should try it when our tenant moves out. The price is up in Portland, but the condo price is still lagging behind. It’s probably not the best time to sell yet.
    If CA housing market is slowing down, Portland will probably follows soon. That’s my experience…

  25. Mr. Tako @ Mr. Tako Escapes

    What a great way to make a decision! I’m glad it all worked out really well too!

    Holding onto real estate for a long time is really the only way to go. Paying those agent commissions is a real killer!

  26. What a great way to make your decision! I love the competitiveness of it, too. I’m really glad you found a renter and that you’ve decided to keep the property. In the long run, that seems like the better choice to me. Congrats on finding good renters!

  27. Definitely! Glad you didn’t “sell your baby” and this is definitely a win-win! One thing I wanted to point out after all the great comments on the “Make Better Decisions” post I wrote for you – I did add a “Quantitative” chart to the decision-making process and it weights the goals based on importance. I think those might help readers who wanted to see the “numbers”. I also combined the charts into a “Mixed Methods” chart too! I ended up using that chart (with both words and numbers) for my big decision. The chart told my “story” and showed the “magnitude of difference” between the choices. I am emptying out my office later this week! Here is a link to the post with those charts.

  28. The Green Swan

    Great read once again. I love the comment and realization you make… you’re getting soft in early retirement. I can see how that would be easy, but stay strong! Glad it all worked out with finding new renters, keeping your place (which seems to be special to you) and increasing rent. It’s a win-win-win! Would love to see pictures of the place too, will you share?

    The Green Swan

  29. Apathy Ends

    I think you made the right choice! If you get another 2-4 years out of these tenants you can setup round 2 against the real estate agent, if you maintain the property (which we know you do) then I doubt you will run into many issues!

    It would feel pretty awesome to have a 1 million check in hand.

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