What is the most expensive landlord mistake you've made?
Member since 2026 · 3 posts · 4 votes
What is the most expensive landlord mistake you've made?
Most Popular Reply
Real Estate Broker · Hyde Park Tampa, FL · Member since 2019 · 2k+ posts · 3k+ votes
6moThis: according to the American Apartment Owners' Association the #1 reason why landlords fail is:
Failure to manage to the lease.
The lease rules.
I would also offer this: Never forget that you're running a business. Tenants will attempt to make their problems yours - they need to pay the rent late, they have to smoke - have to, more. And, if you make one exception, they will test to see if you'll do it again and again and again. Don't start.
33 Replies
- 6moBen ScottPro MemberProperty Manager · Oklahoma City, OK · Member since 2019 · 577 posts · 351 votes
My biggest mistake in the early day was thinking with my heart and not my head. Believing a prospect's sob story and thinking I was being a good person by helping them out. Those are the people that will burn you.
Also, paying for materials for a fence with a vendor I hadn't used before. He took the materials back and cashed in the difference. I called his wife, who had referred me to this vendor, and she told me I shouldn't have trusted her husband. LOL.
- 6moAlexis DeAngelisBusiness MemberProperty Manager · Raleigh, Raleigh-Durham area · Member since 2025 · 51 posts · 38 votes
Good morning,
The most expensive mistake occured during covid when the eviction moratorium was in play. We had residents that knew they couldn't get evicted, so refused to pay for months which turned into over 18 months. By the time we were able to file for eviction and get them out, there balance was well over $40,000. Nowadays, I think the biggest thing for us is requiring renters insurance. With renters, a lot of "liability and damage" is covered, so we use this often to re-coup expenses.
I've also found that doing the tedious maintenance on appliances and HVAC really does make a difference. Spend some now to save more later (if that makes sense).
Good luck with everything and I hope this helps :-)
- Member since 2024 · 158 posts · 88 votes6mo
@Alexis DeAngelis can you make claims against their insurance?
- Property Manager · San Diego, CA · Member since 2026 · 13 posts · 11 votes6mo
Quote from @Alexis DeAngelis:
Good morning,
The most expensive mistake occured during covid when the eviction moratorium was in play. We had residents that knew they couldn't get evicted, so refused to pay for months which turned into over 18 months. By the time we were able to file for eviction and get them out, there balance was well over $40,000. Nowadays, I think the biggest thing for us is requiring renters insurance. With renters, a lot of "liability and damage" is covered, so we use this often to re-coup expenses.
I've also found that doing the tedious maintenance on appliances and HVAC really does make a difference. Spend some now to save more later (if that makes sense).
Good luck with everything and I hope this helps :-)
Ouch, $40,000! We were super lucky and not a single tenant missed rent during covid.
- 6moAlexis DeAngelisBusiness MemberProperty Manager · Raleigh, Raleigh-Durham area · Member since 2025 · 51 posts · 38 votes
Quote from @Allison Park:
@Alexis DeAngelis can you make claims against their insurance?
Yes for most of it 😃
- Real Estate Broker · Hyde Park Tampa, FL · Member since 2019 · 2k+ posts · 3k+ votes6mo
This: according to the American Apartment Owners' Association the #1 reason why landlords fail is:
Failure to manage to the lease.
The lease rules.
I would also offer this: Never forget that you're running a business. Tenants will attempt to make their problems yours - they need to pay the rent late, they have to smoke - have to, more. And, if you make one exception, they will test to see if you'll do it again and again and again. Don't start.
- 6moJaron WallingPro MemberRental Property Investor · Indianapolis, IN · Member since 2018 · 4k+ posts · 4k+ votes
Quote from @Patricia Steiner:
This: according to the American Apartment Owners' Association the #1 reason why landlords fail is:
Failure to manage to the lease.
The lease rules.
I would also offer this: Never forget that you're running a business. Tenants will attempt to make their problems yours - they need to pay the rent late, they have to smoke - have to, more. And, if you make one exception, they will test to see if you'll do it again and again and again. Don't start.
This.
We had a tenant that started parking a car in the yard. I noticed it and texted her that day to remove it. It's in our lease "no vehicles, trash, or debris in the yard". Tenants cannot ignore the lease otherwise things slide and the landlord is out of control. I don't claim to be a PM expert but a business is not charity when it comes to rentals. That's the distinction between successful PM and ones that fail.If a tenant is testing you test them right back and mention the lease. If they don't like they can move out. End of story.
- 6moKerlous TadresBusiness MemberRealtor · Columbus, OH · Member since 2023 · 1k+ posts · 1k+ votes
@Luis Martinez, My most expensive mistake was rushing to fill a vacancy and “giving someone a chance” instead of sticking to strict screening. From my experience, set clear approval rules (income, rental history, background), verify everything yourself, call the last landlord, and never hand over keys until the deposit and first month have fully cleared.
Kerlous Tadres | Reafco Real Estate540 Reviews- Member since 2026 · 3 posts · 4 votes6moTHIS right here is the key! Calling past landlords is now part of my strategy.
Quote from @Kerlous Tadres:
@Luis Martinez, My most expensive mistake was rushing to fill a vacancy and “giving someone a chance” instead of sticking to strict screening. From my experience, set clear approval rules (income, rental history, background), verify everything yourself, call the last landlord, and never hand over keys until the deposit and first month have fully cleared.
- Honolulu, HI · Member since 2008 · 3k+ posts · 2k+ votes6mo
The theme so far seems to be "Nice Guys and Gals Finish Last".
Develop solid processes for each major element of your RE path. Stick to the process. No exceptions, until and unless you have verifiable proof that someone died. If you want to "help" someone, including family or friends, send them a check. That way you will not be paying for damages and court costs on top of your "help".
- Member since 2022 · 1k+ posts · 1k+ votes6mo
Using the same lease for all properties. Each property now has a lease that details extensive rules that are particular to that property.
- Honolulu, HI · Member since 2008 · 3k+ posts · 2k+ votes6moWhy did you decide to draft different agreements for each property, rather than simply adding a set of "House Rules" as a separate, referenced, addendum for specific properties?
Quote from @Henry T.:
Using the same lease for all properties. Each property now has a lease that details extensive rules that are particular to that property.
- Member since 2022 · 1k+ posts · 1k+ votes6mo
Quote from @Richard F.:
Why did you decide to draft different agreements for each property, rather than simply adding a set of "House Rules" as a separate, referenced, addendum for specific properties?Quote from @Henry T.:
Using the same lease for all properties. Each property now has a lease that details extensive rules that are particular to that property.
Are all of your properties exactly the same? Mine are not. The list is long. Take parking for example. If one property has three houses on it, parking must be specific and exactly assigned. Visitors park on street only. No cars under repair or on blocks. Must be licensed and operational. No dead cars allowed. etc. If it's a single house, parking is still laid out and the number of vehicles allowed and where. You think it's your house? It's not, it's mine and you will follow my lease and rules. Otherwise move on. Storage, parties, keep the yard neat, internet, water, garbage cans placement, winter care, blah blah. I don't want any problems and I've found it's better being proactive. I take pride in how my properties look, my neighbors definitely appreciate it. I'm sure many have single lease fitting all of their properties but I haven't figured out how to do that, and my way has really kept things steady after many years doing biz. There is a general part one(applicable to local law) followed by multiple pages of part two.
- Honolulu, HI · Member since 2008 · 3k+ posts · 2k+ votes6mo
Quote from @Henry T.:
Quote from @Richard F.:
Why did you decide to draft different agreements for each property, rather than simply adding a set of "House Rules" as a separate, referenced, addendum for specific properties?Quote from @Henry T.:
Using the same lease for all properties. Each property now has a lease that details extensive rules that are particular to that property.
Are all of your properties exactly the same? Mine are not. The list is long. Take parking for example. If one property has three houses on it, parking must be specific and exactly assigned. Visitors park on street only. No cars under repair or on blocks. Must be licensed and operational. No dead cars allowed. etc. If it's a single house, parking is still laid out and the number of vehicles allowed and where. You think it's your house? It's not, it's mine and you will follow my lease and rules. Otherwise move on. Storage, parties, keep the yard neat, internet, water, garbage cans placement, winter care, blah blah. I don't want any problems and I've found it's better being proactive. I take pride in how my properties look, my neighbors definitely appreciate it. I'm sure many have single lease fitting all of their properties but I haven't figured out how to do that, and my way has really kept things steady after many years doing biz.
Nothing wrong with being proactive, I'm a fan. It is always cheaper to be Proactive rather than Reactive. But most properly drafted agreements have multiple sections to fill in manually with some of the finer details, such as parking assignments quiet hours, allowable Guest visitation periods; and a variety of property, or individual unit, specific details. OTOH many of the items you note above are common across many properties, and those are what we have incorporated into a separate House Rules document. We also provide, via separate document, individual Policies such as Assistance Animal Policies, Move out Cleaning Requirements, and documentation to be completed for all vehicles to confirm ownership, current registration and insurance. - Member since 2022 · 1k+ posts · 1k+ votes6mo
Quote from @Richard F.:
Quote from @Henry T.:
Quote from @Richard F.:
Why did you decide to draft different agreements for each property, rather than simply adding a set of "House Rules" as a separate, referenced, addendum for specific properties?Quote from @Henry T.:
Using the same lease for all properties. Each property now has a lease that details extensive rules that are particular to that property.
Are all of your properties exactly the same? Mine are not. The list is long. Take parking for example. If one property has three houses on it, parking must be specific and exactly assigned. Visitors park on street only. No cars under repair or on blocks. Must be licensed and operational. No dead cars allowed. etc. If it's a single house, parking is still laid out and the number of vehicles allowed and where. You think it's your house? It's not, it's mine and you will follow my lease and rules. Otherwise move on. Storage, parties, keep the yard neat, internet, water, garbage cans placement, winter care, blah blah. I don't want any problems and I've found it's better being proactive. I take pride in how my properties look, my neighbors definitely appreciate it. I'm sure many have single lease fitting all of their properties but I haven't figured out how to do that, and my way has really kept things steady after many years doing biz.
Nothing wrong with being proactive, I'm a fan. It is always cheaper to be Proactive rather than Reactive. But most properly drafted agreements have multiple sections to fill in manually with some of the finer details, such as parking assignments quiet hours, allowable Guest visitation periods; and a variety of property, or individual unit, specific details. OTOH many of the items you note above are common across many properties, and those are what we have incorporated into a separate House Rules document. We also provide, via separate document, individual Policies such as Assistance Animal Policies, Move out Cleaning Requirements, and documentation to be completed for all vehicles to confirm ownership, current registration and insurance.yup. Many items are the same and transferable to other properties, some not. In the early days , When it was easier to remove a dead beat, my lease was one or two pages, now we're 50 pages plus.. Lease renewal is mandatory in Seattle. So I add every little thing I can think of to make sure they toe the line, and then some. I've had people drying their fish on the roof. Sets of ratty furniture in the front yard for hanging out. Rock band building a practice room in the living room. etc. I've learned and continue to get ideas from others here. Sadly, as my lease is the best its ever been I'm about ready to get off the merry go-round. Seattle is absolutely toxic, and the rest of WA state is very pro-tenant. I'd leave if it were just me. I'm winding down just fine.
- 6moDrew SygitBusiness MemberProperty Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
Two thoughts:
1) Not having SOPs
If you don't have a plan to succeed, you often default to failure.2) Delays in not following your SOPs
Have guardrails built into your SOPs to limit empathy urges.
Logical Property Management4.9458 Reviews - Member since 2011 · 152 posts · 113 votes6mo
My biggest mistake financially with my rentals was not having the properties sufficiently divided between property insurance policies. When I had a second (sizeable and legitimate) claim, they understandably raised my rate. The issue was that the rate got raised on ALL the properties on the policy for several years until I could get them back down even though those properties had nothing to do with the claims.
You are referring to the 25th annual MrLandlord.com national convention with Jeffrey Taylor in Columbus. Last year it was in Indianapolis, and I was one of the featured speakers. It's a very worthwhile event with a different theme each year.
- Member since 2026 · 3 posts · 4 votes6mo
Quote from @Joel Miller:
My biggest mistake financially with my rentals was not having the properties sufficiently divided between property insurance policies. When I had a second (sizeable and legitimate) claim, they understandably raised my rate. The issue was that the rate got raised on ALL the properties on the policy for several years until I could get them back down even though those properties had nothing to do with the claims.
You are referring to the 25th annual MrLandlord.com national convention with Jeffrey Taylor in Columbus. Last year it was in Indianapolis, and I was one of the featured speakers. It's a very worthwhile event with a different theme each year.
Thank you, Joel! Your insights are very much appreciated. I am also currently having the same issue with my properties insurance policies. Mine got raised as well after a claim, which is understandable in this case. Mix that with actual insurance hikes and it I quite a headache.
Also, thank you for letting me know about the convention. I am now planning to attend!
- 6moColleen F.Pro MemberInvestor · Narragansett, RI · Member since 2013 · 8k+ posts · 4k+ votes
@Luis Martinez my most expensive mistake was not kicking my 7 year tenants out when things started to go wrong. They left after 2 months of promising to catch up. I got in there and there were burn marks on the wood floor from them falling asleep in the recliner. They had always kept things nice. I think I probably should have gone in sooner when I saw their health failing as they were not supposed to be smoking in the house anyway. One was stage 4 cancer and the other in failing health. I think we just could have made an agreement to leave with them sooner that would have decreased my costs. The next landlord never called me for a reference and I bet they took it worse than me.
- Real Estate Agent · Memphis · Member since 2026 · 558 posts · 326 votes6mo
For me, the biggest one was accepting a “mostly qualified” tenant to reduce vacancy. On paper they were close enough, and it felt like a reasonable compromise at the time. It turned into months of late payments, constant follow-ups, and eventual turnover costs that far outweighed a few extra weeks of vacancy.
That experience really reinforced that standards only work if they’re consistent. The moment you start making exceptions, you’re usually taking on risk you don’t fully see yet.
On the event side, conferences can be valuable, but the real benefit tends to come from practical systems and conversations with operators, not just presentations. If it’s focused on real-world case studies and how people structure their processes, that’s usually where the value is.
- Rental Property Investor · Denver, CO · Member since 2026 · 8 posts · 6 votes6mo
Skipping a structural inspection on my second duplex. Inspector noted some minor cracking as 'typical settling' and I didn't push for a second opinion because I wanted the deal to close. That property is now showing foundation movement and the quotes are $15-25K to fix it properly. I bought it in 2017 and it's been cash flowing fine so the deal still worked out, but I'm sitting on a repair I can't ignore forever.
I pay for a structural engineer on any 1960s-or-older property or anything in an area known for clay soils now. $400-500 and it's already talked me out of two deals where the general inspection said everything was fine.
- 6moColleen F.Pro MemberInvestor · Narragansett, RI · Member since 2013 · 8k+ posts · 4k+ votes
@Henry T. yes and I didn't think I would have to tell someone they couldn't hang their boat engine from a tree, common sense right? Haven't had any fish drying just pot. It is scary how unbalanced the landlord tenant relationship is becoming.
- Property Manager · Calabasas, CA · Member since 2026 · 141 posts · 67 votes6mo
On the commercial side, my most expensive mistake was missing the window to audit a CAM reconciliation for a full lease year. Had a retail tenant who pushed back on their annual reconciliation — not because the numbers were wrong, but because they suspected the management fee we were passing through was higher than what the lease allowed. I didn't dig into it for several months because everything else was running smoothly and I assumed our numbers were clean.
Turns out we had been grossing up the management fee on a modified gross lease that had a specific cap on pass-throughs. Not a massive dollar amount, but enough that we had to retroactively credit the tenant, and the goodwill damage with a tenant we wanted to renew was real.
Patricia's point about managing to the lease is exactly right — and in commercial it applies just as much to what you're charging as what you're enforcing. CAM leases are full of provisions that are easy to miss if you're not actively reconciling against the actual lease language each year, not just running the numbers from last year's template. That audit discipline is the thing I didn't have early on that cost me.
- Honolulu, HI · Member since 2008 · 3k+ posts · 2k+ votes6mo
Here are a couple of examples, not actually OUR mistake, but definitely the Condo Board and previous PM's (they went through several over a 5 year period) missed them. Both on same property.
Elevator Maintenance Contracts. These are the lawful equivalent of Highway Robbery anyway, but the National companies that provide most of the service have contracts with a bizarre renewal process on a typical five year contract. There is a narrow window, 30 or 45 days, which ends six months before the end of the contract. Of course the procedure is buried deep in the very lengthy, very fine printed, contract. Very easy to miss, and they have no flexibility once the contract is signed. The renewals are just extensions, also 5 year, so that requirement continues as original.
Cell Phone Antenna Arrays/Towers. Very similar to the Elevator Contracts, except even longer term, the one I was looking into was 30 or 40 years initially, with the Cell companies actually changing several times, but maintaining the original very, very, cheap, lease rate. The antennas themselves were on the roof of the building, mounted to large pipe frames weighted down with sizeable stacks of concrete blocks. Roof was flat, modified bitumen so they were not allowed to penetrate it.
- Property Manager · Calabasas, CA · Member since 2026 · 141 posts · 67 votes6mo
Richard, the elevator contract example is a perfect illustration of what I'd call the "fine print trap" in commercial operations — where the mistake isn't bad judgment, it's just not knowing a specific clause exists.
The cell tower lease issue is even more painful because those long-term rates can stay locked for decades while the asset value and carrier revenue go way up. I've seen a few buildings where the antenna lease was essentially invisible to successive owners because it never showed up as a problem — it just quietly underperformed relative to market. You only discover the gap when you try to renegotiate and find out there's a 30-year term with automatic renewals and no termination right.
For anyone acquiring commercial property: requesting estoppels and a full lease abstract on every contract — not just tenant leases but service contracts, rooftop licenses, parking agreements — is worth the extra due diligence time. The ones that bite you are usually the ones nobody flagged because they looked routine.
- Investor · Houston, TX · Member since 2019 · 95 posts · 29 votes6mo
Luis — most expensive mistake across 100+ transactions in Houston wasn't a bad tenant or a blown rehab budget. It was not having a capital system in place early enough.
Early on I funded everything through banks and hard money. Every surprise — busted sewer line, tenant trashes the place, deal needs more rehab than expected — meant scrambling for money at the worst possible time. That scramble cost me more in bad decisions than any single tenant ever did.
The fix that changed everything: I started building cash value inside a whole life insurance policy. Now when a $20K surprise hits, I borrow against my policy in days. No bank, no credit check, no 12% hard money. My cash value keeps growing even while the loan is out. And my family is protected with a death benefit the whole time.
Patricia nailed it — manage to the lease. But I'd add: make sure you have capital access that doesn't depend on a bank's mood when you need it most. The expensive mistakes aren't the ones you can predict. They're the ones that hit when you're already stretched.
- Property Manager · OK · Member since 2024 · 98 posts · 74 votes6mo
In my case, the costliest mistake was renting to a tenant because they had a substantial lump sum of cash but with poor background check. Their prepaid rent for one year should have raised concerns about their background history which I chose to ignore until they stopped paying rent and I had to spend six months in court and thousands in legal fees. It made me learn that short-term cash could not replace a reliable stable income and a clear rental history.
- 6moMaranda TuckerPro MemberProperty Manager · Charlotte, NC · Member since 2022 · 152 posts · 118 votes
Working with over 200+ investors here in Charlotte, one of the most common and most expensive mistakes I see is not the nightmare tenant..
It is setting rent based on what you need the property to cash flow instead of what the market will actually pay.
Example: an investor lists at $1,400 because that's what their mortgage math requires. The unit sits for 30–45 days. They eventually lease at $1,275 anyway — but now they've also eaten a full month of vacancy. That's not a $125/month haircut. That's $1,275 in lost rent plus carrying costs during the vacancy. The "higher" price actually cost them more money than if they'd priced it correctly on day one.
The compounding part is what most people miss. A vacant unit doesn't just cost you rent. It costs you leasing time, showing coordination, re-listing energy, and — if you get desperate enough — you start loosening your screening criteria to fill the unit. That's how the "bad tenant" story actually starts. Vacancy pressure leads to a screening shortcut, which leads to the $5,000–$10,000 loss everyone talks about. The root cause was the pricing decision weeks earlier.
The mortgage payment is not the market's problem. Price for the market, screen without pressure, and the expensive mistakes mostly go away.
- Property Manager · San Diego, CA · Member since 2026 · 13 posts · 11 votes6mo
Trying to help someone out. "She's so nice. I'm sure she'll pay her rent." I learned my lesson a long time ago. I stick with my rental criteria, no matter their sob story.
I just turned someone down this morning because of her terrible credit. She's going through a divorce, yada yada. Doesn't matter. I don't want to deal with the inevitable eviction. - 6moJ CastroBusiness MemberLender · Florida · Member since 2025 · 684 posts · 246 votes
Hey @Luis Martinez, welcome to BP!
That’s a great question—most of us definitely learn the hard way at some point.For many investors, the most expensive mistakes usually come down to poor tenant screening or underestimating rehab/maintenance costs. One bad decision there can wipe out months (or years) of cash flow.
As for the National Landlord Convention 2026, events like that can be really valuable—especially for networking and picking up systems from more experienced operators. If you’re looking to grow and avoid costly mistakes, it’s likely worth attending at least once.
- 6moCameron TopePro MemberProperty Manager · Katy, TX · Member since 2015 · 1k+ posts · 1k+ votes
Quote from @Luis Martinez:
I’ve been thinking about this recently because it seems like most landlords (myself included) learn things the hard way.
For me, one bad tenant ended up costing thousands between missed rent and repairs. Curious what others here have experienced, what’s the most expensive mistake you’ve made as a landlord?
Also, I came across the National Landlord Convention happening June 4–6, 2026 in Columbus, Ohio, and it looks like they focus heavily on learning from real landlord mistakes and systems. Has anyone here attended before?
Would love to hear if it’s actually worth it.Blindly trusting contractors.
Trust, but verify.
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