The older I get, the more I dislike being a landlord. There’s too much potential for disappointment, misunderstanding, or outright unpleasant moments. When you’re dealing with people and one of your most valuable assets, the margin for frustration is high.
If you want to be a successful landlord—and not get run over—you need to set expectations clearly and enforce them. Otherwise, you’ll constantly feel like you’re letting someone down or, worse, being taken advantage of.
This post is part of a series chronicling my journey as a landlord since 2005. My goal is to give readers a clearer picture of what’s really involved if you’re considering becoming one yourself. This latest experience also underscores the value of hiring a property manager: someone emotionally removed from the process who can treat your property purely as a business asset.
San Francisco’s Hot Rental Market
After 20 years of being a landlord, I’ve experienced all the cycles. And right now, the San Francisco rental market is strong. With home prices near all-time highs, mortgage rates still elevated, and the ongoing AI boom creating more jobs, demand for rentals seems to be increasing.
Earlier this year, my tenants of five years gave notice. That meant I had a chance to test the waters again and re-rent my house. This time, the whole house to optimize our passive income, not just the upstairs while keeping the downstairs empty. I listed it on Craigslist on a Tuesday and was immediately bombarded with interest.
By Saturday, I hosted two private showings for excellent prospective tenants. Both groups wanted the place on the spot. One wife was so excited she literally shouted: “We’ll take it! I want to move in right now!” when she was leaving.
These weren’t flaky candidates either. They were organized, enthusiastic, had great jobs, and excellent credit. It was difficult to choose between them, so I asked each to submit their best offer. Within 10 days, I had selected the tenants, collected the deposit, and received the first month’s rent.
Everything was moving smoothly. Or so I thought.
Preparing the House for New Tenants
Because my wife and I were genuinely excited about this family, we went the extra mile to prepare the home. Over two weeks, we painted walls and trim, patched and sanded uneven spots, scrubbed everything top to bottom, and tackled a massive amount of yard work. It felt more like we were prepping the house for sale than for rent.
Our previous upstairs tenants had been solid, but they neglected the yard. So my kids and I rolled up our sleeves and got to work reseeding, trimming bushes, pulling weeds, and watering everything back to life. Doing property maintenance alongside my kids is something I plan to keep up. It builds their work ethic, gives them hands-on knowledge, and helps them appreciate the value of taking care of what you own. Working with them also makes me more enthusiastic about addressing issues.
On top of that, because the prospective tenants wanted to move in as soon as possible, I had to work out an earlier exit with the current upstairs tenants. That meant negotiating a prorated rent, agreeing on a comfortable move-out date, and making sure they returned the unit in its original condition. Not easy handling both sides! In the end, it all came together. I got the new family in eight days ahead of schedule. By move-in day, the house looked fresh, clean, and ready to be enjoyed.
There’s a unique satisfaction in handing over a property in pristine condition. It sets the tone for the relationship right away. You hope the tenants will see the pride of ownership and reciprocate by taking care of the place. And as a landlord, it’s also a mental reset. You feel good knowing the property is in great shape before handing over the keys once more.
The Move-In Demeanor Shift
On move-in day, the husband arrived early for our walkthrough. Calm, polite, and well-prepared, he had scheduled out the day:
- Walkthrough with me at 10 a.m.
- Friend arriving at 11 to help unload a van of more delicate items the tenant brought.
- Main movers coming at 11:30 with a large truck.
Everything about him was orderly and respectful.
The wife showed up later, around 11:15, clearly stressed from the packing and logistics at their old place. The joy she’d shown when she shouted, “I want to move in right now!” was nowhere to be found.
When I greeted her with a smile and a “hello,” she barely looked up. No big deal, I told myself—this is a business transaction, not a friendship. Moving is stressful and a lot must have been on her mind.
I wrapped up the walkthrough, explained all the nuances and maintenance tips about the house, handed over the keys, and wished them the best.
The Surprise Request
A week later, I happened to be driving by and saw them outside working in the yard. This was encouraging. I pulled over to say “hello,” and quickly grab a hot tub stool and some chlorine bottles I’d left in outdoor storage.
The husband was friendly, asking how I was doing. But the wife immediately hit me with:
“Hey, I’ve got a question for you. Can you get some mulch and you pay for it? There are some bare spots here and especially in the back.”
No “hi.” No “thanks for the clean yard” or “the house is great.” Just a request.
Her tone caught me off guard. I expected some acknowledgment of the work we’d already done. Or at least how she was enjoying the place. Instead, I felt like an employee being given a directive, something I am no longer accustomed to after retiring in 2012. All those hours my kids and I had spent reseeding, trimming, and watering? Apparently meaningless or not good enough to their standards.
I muttered a noncommittal, “Maybe,” and left with a “good-bye” for good measure. I needed time to think about her request after the lease was signed.
Setting Clear Expectations
I pride myself on providing a great product for the rent people pay. That’s why I was a little surprised by her request, and also why hiring a property manager helps with reducing emotional attachment.
My lease—which I’ve been refining since 2005—is multiple pages long and very clear. Nowhere does it say the landlord must provide mulch. In fact, it explicitly states tenants are responsible for maintaining the yard and plants.
During the private showing, they never mentioned mulch. During lease review and edits, mulch never came up. Only after signing did this “expectation” surface. Between signing the lease and moving in, the mulch didn’t suddenly disappear in this short period of time.
This is exactly why setting clear expectations is so important. If something isn’t in the lease, it shouldn’t suddenly become a requirement.
The Slippery Slope Of Giving In
Here’s the danger: once you start giving in to extra requests, expectations balloon.
If you buy and spread mulch, what’s next—a Toto Washlet and new light fixtures at your expense? The list of wants can be endless. For instance, my new tenants also asked me to cover the cost of custom paint they used in a downstairs office and bedroom. I declined. The existing paint was perfectly fine. I had just repainted one of those rooms myself. Aesthetic upgrades fall squarely into the category of tenant expenses.
Tenants are free to ask, but landlords need to protect themselves and are free to also say no. If you oblige every request, you risk blurring the boundaries. Your role shifts from owner to on-call service provider. That semi-passive income starts turning into active income, which is what you want to avoid.
And when your profit margins are already squeezed by property taxes, mortgage interest, maintenance, and the occasional late rent, doing unpaid “extras” can tip your rental into unprofitability.
Worse than the money is the mental energy drain. Once you establish yourself as a landlord who always says yes, saying no later becomes much harder. Remember, as someone seeking financial independence, your assets must work for you, not the other way around.
Finding A Compromise
After sleeping on it, I decided to offer a middle ground. I emailed the husband—who had been polite and professional from the start—and told him I’d reimburse up to $150 for mulch. They could pick it up themselves and spread it around. At roughly $9 a bag, that would cover about 15 bags after tax, which felt reasonable.
This way, I wasn’t setting the precedent of becoming their personal landscaper, but I was still showing some flexibility. To make things easier, I even told them which store to go to and exactly where to find the mulch in the store. It was a small gesture, but I wanted to start the relationship off on the right foot with a little give. A little goodwill in the beginning can go a long way over the course of a tenancy.
They accepted right away and seemed genuinely thankful. As it turns out, at their last rental, the landlord expected them to mulch the garden every single year, so they assumed that was standard.
I explained that I hadn’t noticed the bare spots enough to make it part of the lease, but since they brought it up, I was fine with refreshing it every couple of years if needed. I even suggested they spray some Rock Glue to help keep the mulch in place and told them I’d cover the cost of that too.
In the end, what could have been a sticking point turned into a small win-win. They will get the spruced-up yard they wanted, and I got peace of mind knowing we’d started our landlord-tenant relationship with a little cooperation instead of conflict. The $150 in mulch is not a big deal at all. It's all about setting expectations and asking respectfully.
I’m confident they’ll turn out to be great, caring tenants. After all, great tenants care about the yard and curb appeal, which is way better than not caring at all. In the beginning, it’s always just a leap of faith. And I've got faith that after 20 years of being a landlord, these new tenants will be terrific.
Why Strict Rules Build Better Relationships
Think back to school. Remember the strict teacher who laid out rules from day one? At first, you thought she was harsh. But by the end of the year, she was your favorite teacher. Why? Because the rules were clear, fair, and consistent.
After three years of coaching boys’ high school tennis, I’ve learned the importance of establishing clear rules too. If you don’t enforce them with firmness, teenagers will quickly test boundaries and disregard your authority.
The same principle applies here. Clear rules create mutual respect. They just need to be reviewed and understood by both parties.
If you’re a tenant: read the lease carefully, ask questions before signing, and clarify expectations upfront.
If you’re a landlord: review the lease line by line, highlight tenant responsibilities, and give tenants several days to raise questions. Ask them if they have any other concerns that is not in the lease. You must be as thorough as possible. Keep improving upon your lease for next time.
That small effort on the front end can save you enormous frustration down the road.
Why I’m Reducing My Landlord Exposure
Interacting with people can be draining, especially when expectations don’t line up or the requests feel unreasonable.
Here's another example. My old tenants wanted me to buy three light fixtures they had installed. I declined. I had already been flexible in letting them swap out the original fixtures, so I told them they could either leave their new ones behind or reinstall mine. They had packed both my old curtains and light figures in boxes in the garage, and they were taking up space.
They weren’t thrilled with my answer and then asked me for the new tenant’s contact info to pitch them on buying the light fixtures. I found the whole exchange draining over potentially a few bucks. I never would have asked my landlord to purchase light fixtures I chose for myself. Maybe it was a cultural difference. But to me, it just felt like another reminder of how mismatched expectations can create unnecessary friction.
If I had simply stuck to the rules and said no to swapping out the original light fixtures, this conflict wouldn't have taken place. But this is what you sometimes get for trying to be flexible and nice.
Although owning rental properties is one of the best ways to build wealth and secure retirement, I’ve reached the point where the constant hassles outweigh the rewards. Each turnover requires managing departing tenants, handling an exit walkthrough where damage always shows up that they have “no idea” what happened, finding and vetting new tenants, preparing the property, and then repeating the walkthrough process. It’s a demanding cycle, and after years of managing it, I’ve decided enough is enough.
I can't wait to sell another rental property in a couple of years, as by then, I will qualify for the tax-free exclusion rule once more.
Landlording Can Be Like Working A Corporate Job
One of the main reasons I left corporate America was due to people. Office politics, difficult personalities, and constant requests wore me down after 13 years. I didn't like managing people either as I want more people to be free to do as they please.
Being a landlord is often no different. Even with supposedly “perfect” tenants, issues arise. That’s why, even though I’m still bullish long-term on San Francisco real estate, I accepted a preemptive offer in 2025 for my old primary residence that was a rental for one year.
I reinvested 100% of the proceeds into the S&P 500, individual stocks, Treasury bonds, and venture capital—investments that require zero people management. Shifting semi-passive rental income into truly passive investments has been a relief.
Once you FIRE, you might also decide you don’t want to manage rental properties either, for many of the same reasons you left your job in the first place.
Lessons Learned For Landlords
Here are the main takeaways from this experience:
- Set clear expectations upfront. Your lease is your rulebook. Don’t rely on verbal understandings as it opens yourself up to misunderstandings.
- Don’t change the terms midstream. If it’s not in the lease, it’s optional, not mandatory.
- Be careful with “extras.” Once you start saying yes, tenants may keep asking for more.
- Protect your margins. Expenses creep quickly; don’t let small favors turn into big, ongoing obligations.
- Respect goes both ways. Kindness and courtesy matter. Tenants who treat you well deserve more flexibility than those who don’t. Use your emotional intelligence to make life easier for both sides.
In my next lease agreement, I plan to spell out more details around exterior maintenance, clarify that the property is rented “as is,” and specify that tenants may make improvements or aesthetic changes only with prior approval and at their own expense.
The path to building a livable passive income stream for financial freedom isn’t easy. The key is to always learn from each experience so the next one becomes a little better.
Let's All Understand And Follow The Lease
At the end of the day, both landlords and tenants want a positive experience. Tenants want value for what they pay. Landlords want tenants who care for the property and are self-sufficient. Neither party wants to keep going back and forth with each other during the entire time of stay.
This balance is achievable, but only when both sides clearly understand and follow the lease. Without expectations, frustration grows. With them, the relationship has a real chance of succeeding.
Landlords, have you ever had tenants ask for things that went beyond the lease? How did you handle it—did you accommodate, push back, or find a middle ground? And tenants, I’d love to hear your side too. Have you ever convinced a landlord to go above and beyond what was in your lease? If so, how did you pull it off?
At the end of the day, I think setting expectations is the foundation of a smooth landlord-tenant relationship. But I’m curious—how important do you think it really is, and where do you draw the line?
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I’ve personally invested over $450,000 across multiple Fundrise funds and several accounts, and they’ve been a long-time sponsor of Financial Samurai. With the Fed cutting rates again and three years of underbuilding due to high financing costs, I expect to see continued upward pressure on rents in the years ahead.
I have had tenants ask for things that went beyond the lease. I said yes to a few requests because they would enhance the value of the property. For example, I said yes and covered the costs of replacing a mirror in a small bathroom with a medicine cabinet to increase storage. A tenant asked me to update the landscaping and I took a similar approach to yours: I told them to send me a plan of what updates they would like to make, and if it’s reasonable, I’ll cover the cost of their materials. Nothing happened with that. I have the hardest time with repairs – one tenant keeps clogging drains, breaking the disposal, and breaking appliances, and the repairs add up. I covered the most recent repairs with a firm note that, per the lease, the cost of any future repairs caused by their negligence will be their responsibility. I’m getting tired of dealing with tenants. It can be a lot of work on top of a full-time job and raising kids.
I’ve been a landlord for 11 years now. I have three properties that cash flow at least $2k each per month. They’ve all appreciated nicely as well. But I’ll tell you, I am getting tired of the grind of turnover and having to find new tenants. It’s a significant stressor that hangs over my summer’s. This past summer was the first time I seriously considered selling them. However, now is not a great time to sell in my area and I would be giving up 2.9% 30 year fixed mortgages. I’m trying to stay strong and hang on for another 10 years. Then I’d like to package them into a 1031 exchange for a house in Hawaii. Gotta keep hope alive!
Yes, hang tough! Being a landlord is a war of attrition. The longer you can hold on, the better usually. Now is absolutely the wrong time to sell, right before another series of Fed Fund cuts over the next two years. Hold on!
Got rid of all rentals 3 years ago and sleep well since. Dividends don’t disturb you in the middle of the night about clogged bathrooms, power outages, or falling trees on the property.
As renter’s we have been blessed with extraordinary landlords. They have gone above and beyond for their homes and for us as their tenants. We feel lucky, but to be fair, we are very, very picky in our choosing.
In fact, we typically avoid properties that are managed by companies. We have heard too many stories of mismanagement and have also experienced walk-throughs where it was disturbingly clear that the company did not care for the property like one should. If you want to go with a management company for your rental, do vet them well, perhaps even more intensely than you would a tenant.
Our current landlord plans to downsize into this home when he’s ready. He is the second owner and has done a nice job with the remodel. He was impressed by our questions when we first walked the property with him. Since we’re experienced as tenants and have had lovely landlords in the past, we made sure to include questions regarding expectations and he told us that’s why he chose us over another couple.
We’ve been renting for nearly three years now and have made two requests well outside of the rental contract:
A) A new garage door – original from the 80’s
B) Hurricane shutters for the original 80’s aluminum windows
I can see how both of these seem like incredibly ridiculous requests, but the truth is, they were absolutely necessary. We were cautious to even ask, but he comes every month to collect the rent check (he’s old school) and to clean the A/C drain, so after a several months of getting to know one another, he understood we were looking out for his property and made a plan for them.
The garage door had lost its seal, which was a huge expense to our energy bill and we were tired of the critters getting in – both seen and unseen. Sideways rain also would come in through the gaps, so he recognized the need to protect not only our valuables in the garage, but for health and energy concerns.
As for the windows, we gently asked what his plans were for them and brought to his attention the Florida Window Replacement Grant. We worked together to see if his home qualified, but since it would be a grant for a rental, he could not apply. So, the next best for his budget was to supply us hurricane shutters, which are technically required for homes to have in our county.
We feel very fortunate to be taken care of in this way an any service provider that has come into this home has told us that our rental is in pristine condition in comparison to many of the homes they service. That alone helps us sleep peacefully knowing we with are supporting of his own financial independence journey while we figure ourselves out.
Cheers to great landlords like yourselves and ours!
Thanks for sharing your experience! Glad things have worked out. I think one of the keys is that you demonstrated you were good tenants over several months or years before asking for the garage door and shutters. And that you were friendly and built a relationship. So key, as landlords want to help great tenants who are nice. And not so much tenants who are rude and treat landlords like their employees.
Changing the garage door is a big request if it still works. But given it has holes and stuff, it sounds like a good home upgrade for him too when he moves back in. I’m unfamiliar with hurricane shutters, but if it’s the lawn then they got to be done!
Cheers
That’s key, for sure! Tenants who are not kind to their landlords certainly should not have much in terms of expectations outside of what’s outlined in the contract.
As for the law in our county, I’m certain that the requirement has more to do with home insurance as no governing entity goes around enforcing it, unless its a new-build. This could explain why he was uninspired by the request when we first approached him on the topic and the fact that no hurricane damage has occurred to the home in the ten years under his ownership.
Nonetheless, we’re glad he came around.
Sam, can you think of *any* reason to keep a rental property if it’s certain to be cashflow negative?
Sure. Future price appreciation. If there’s a home price boom, it more than makes up for negative cash flow.
I kept a rental property when I moved out in 2013 that I had purchased in 2007. Even in 2013, it was still worth less than I had paid for it in 2007.
It was slightly cash flow negative (less than $100/month) but the principal on my loan was dropping each month by a few hundred dollars thanks to the tenant paying rent so it still felt like a positive. Held it until 2022 and sold for almost double what I had originally paid in 2007.
Dealing with people was my least favorite part of my last job. It’s complicated, time consuming, and draining when things don’t go as expected or when miscommunications occur, which is often.
And of course every rental, tenant/owner relationship is unique just like the properties and leases. Sometimes things turn out differently than expected on both sides. Hopefully things will smooth out and work out well for the remainder of the lease and beyond!
There is nothing passive about rental income. When I hired a property manager, I just ended up managing the property manager. The management company did not care why anything in the rental broke or how to minimize problems. In fact, it gave them more jobs and revenue sources for their management business.
Yeah, that is what I’m worried about. Just another person to manage on top of the tenants. And then added costs as they spend money on things that can be fixed or done for free.
Another one of my new tenant request was to get the compost bin and garage bins professionally cleaned. I didn’t ask, but I think the assumption was they wanted me to pay for it regularly.
Again, not in the lease. So I went over and I just hosed down the compost bin for five minutes and got all remnants out. And it was totally fine! To spend any money to just wash your own bins with a hose each month sounds unusual to me. But everybody has different standards and expectations that try to be met.
Your previous tenant asking you to buy the light fixtures they installed is comical, especially when you were gracious enough to let them change them to their own taste. What kind of cheap a$$ tenants would ask such a thing?
I’d tell them to hire an electrician and put all the original light fixtures back at their own expense out of defiance, even if the light fixtures are nicer.
People are nuts and so entitled! Being a landlord is no fun. I’ll stick to private real estate, REITs, and stocks instead.
As a former landlord, the article is spot on. Job one is making sure the finances work (applies more to pure rental than this situation). People management is job two though it can make you miserable unless clear boundaries are set. Now, I invest in REITs. Happy to be a former landlord.