7 Tenant Horror Stories That Prove Landlording Isn’t A Job For The Weak

I’ve been around real estate investing for over 10 years now. To say that I’ve made my share of mistakes would be perhaps the largest understatement of my life. When your real estate investing career involves DEA agents, feces on the wall and dead cats, it puts you in the upper echelon of the real estate idiot category or real estate veteran category. I’ll let you decide.

Below is a list of the top 7 craziest stories I have after years of being a property investor:

1. The time the DEA, FBI and ATF called me all at once.

So if you were to dream about a worst-case scenario for rental property it would probably include the following:

  • A tenant not paying rent.
  • Hard-core drugs.
  • The FBI.
  • All three of the above on the news and facebook.

Lucky for me all these scenarios happened at once!

Once again, I had a genius thought that went something like this: “I’m going to hire a property manager to deal with all this crap.”

I told him I’m an easy-going guy with only two rules:

  1. No cats (see above).
  2. Complete a background check.

Well it turns out two rules were two too many for this property manager. Truth be told, I didn’t know what his background looked like either. I never met the guy.

Anyway, one day I’m on the crapper perusing Facebook (like we all do) and I see one of my buddies post the following update on Facebook:

“Woke up to the sound of gunfire. Turns out it was actually the sound of Multi-bank Grenades. Happy Monday.”


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Via reactiongifs.us

2. Cat lady that took crazy to a whole new level.

Fact: If you don’t have a cat story I don’t even consider you a legitimate real estate investor.

One time I had this genius idea that I was going to do everything virtual. I wasn’t ever going to meet the tenant in-person, instead I’d just do everything on my timetable and on the computer. I just finished putting in all new carpet (the old-timers are already laughing) and fixing this unit up. Then I posted some awesome pictures and a video walk-through on Craigslist.

There was this lady that was getting a job transfer as an assistant manager of a restaurant from Atlanta who liked the place. I emailed her a lease and Paypal request (pre-Cozy times) for the first month’s rent and deposit.

She paid-within the next day and I put the keys in a lockbox so she could check herself in. I was a FREAKING GENIUS!

She paid like clockwork for 5 months and I was seriously considering writing a book title: I’m a Real Estate Genius.

Well, after 6 months she stopped paying.

Her response was typical, amazing and existential all at once.

In an email:

Me: Hey I noticed you didn’t pay rent this month. Is everything ok?*No response for 3 weeks.*

Her: Oh yea, I moved out a month ago. I left the place clean but accidentally left my cat.

Me: *&$^#&$!)@#

Want to know what it was like to walk into my recently refurbished apartment after that email? It went a little something like this:

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Via giphy.com

3. The ever-so-slight maintenance problem.

This wasn’t exactly a tenant nightmare but it is one of the craziest situations that should definitely be added to this list.

A lot of people (primarily ones that don’t own rental property) have this utopian dream of owning a couple of free-and-clear rental properties and then retiring to the beach and drinking mai-tai’s between massages. Well, if you’re one of those people, this next “situation” can possibly debunk your dream.

My wife and I rented out the first house we bought together and through a combination of luck, faith, and a 10-year mortgage, it’s paid-off. Literally, the month after we paid it off, a tenant texted me this:

Maria: Hey Jimmy, we’ve got A LOT of rain coming in through the back window. It’s coming through the wall.Me (trying to compose myself): Sorry to hear that, did you call one of the maintenance guys on the list I gave you?

Maria: Yea, none of them have called me back. Can you come look at it?

Me: Sure thing. Again, my apologies.

So I drive over there to look at it. My imagination was running wild with a scenario like this:

house floodingPin
Via giphy.com

Of course, by the time I arrived it wasn’t raining so I couldn’t tell what was going on. The next day I return to put some tarps up with my kids, just to buy some more time to call a few contractors and figure it out.

Side note: Right before we finished, I fell off a ladder and landed pretty much exactly like this:

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Via giphy.com

It took 2 additional weeks for 2 contractors to finally go over there just to assess what was going on and give me an estimate. Meanwhile, the tarps didn’t work and my house continued to flood every time it rained. And as murphy’s law would have it, it rained pretty much everyday.

Why multiple contractors couldn’t figure out what was going on is beyond me. One of them wanted me to rebuild the whole back wall at a measly price of $12,000! Another said he could rebuild part of the back wall for only $2,000. I chose the latter.

Meanwhile the poor tenants had to deal with this for 2 months!

Needless to say, I bought them a ham for Christmas and skipped the trip to the Bahamas.

4. Do you know how to clean blood off the walls?

This was a tenant nightmare I had before buying this particular property.

I was looking at buying 2 duplexes. They were very standard duplexes, all brick and in a nice middle-class area.

Well, during my last walkthough, I noticed a unit was suddenly empty and there was new paint on the walls.

Me: What happened to the tenant?Seller: Oh yea, I didn’t tell you about this unit?

Me: Umm, I guess not.

Seller: Well, it’s the craziest thing. *long pause* Let me ask you, are you a good painter?

Me: Yea, but what happened to the tenant that was just here a week ago?

Seller: Well, it’s the craziest thing. Ever since I owned this place whoever lives in this unit commits suicide. I’ve just gotten used to it. This time, the police just told me to paint the walls after they finish their investigation.

Me: Umm yea. I’m going to need my earnest money back.

I wouldn’t buy that place if Bill Murray himself planned on moving in.

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5. My roommate is insane.

As a landlord, you learn real quick not to judge. Yes, you can ask pertinent questions, but not nosy questions.

There was this young guy and girl that wanted to rent an apartment from me. They both worked at a restaurant. He was a cook, she was a waitress. This was a very typical situation for me.

She was in the middle of a divorce and he was just looking for a place to live.

They showed up to tour the place and handed me first month’s rent and a deposit in cash before I even asked what their names were… literally! I’m not making this up.

In my infinite wisdom, I thought they would be great tenants since they had all this cash.

See where this is going?

Over the next couple months they painted and fixed the place up. I always assumed they were a couple but evidently they weren’t.

(Quick note: Possibly one of my worst personality traits is I feel this need to text people back. It’s a very bad trait when you have crazy tenants.)

One day, she starts texting me, incessantly complaining about him.

I’m in Chicago for a work-trip and she’s texting me over 100 times a day.

  • He’s loud at night.
  • He parties.
  • He stays up drinking.
  • And countless other details.
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Via giphy.com

I couldn’t take it anymore. I told her to call the cops. I suggested she move out. I was fine with her doing anything other than texting me. She wouldn’t though. She just kept texting and texting.

FINALLY, she texted me this:

Her: He’s even having sex with men for money.Me: Really? How much does he charge?

She never texted back and moved out the next day.

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6. The tenants that didn’t give a f***. Wait, technically they did.

One time I rented to a couple who were the types to complain about everything. I had to teach them to make a list and then I would come over once a month and fix everything.

They would complain about things like water pressure or how the blinds hung, etc.

Anyway, one time I went over there to fix everything on the list. Apparently they must have REALLY not liked how the blinds were hanging because the blinds were removed from the front bay window (this window was right in front of the parking area).

When I pulled in the driveway I couldn’t believe what I saw.

They were going at it, butt naked, right there in front of the bay window. And they didn’t stop after noticing me. They just kept going at it.

Luckily I had my mower with me so I just cut the grass.

They “finished” while I was weed eating.

Then the guy comes out with a beer and doesn’t say anything other than thanks for coming over and mowing and fixing stuff.

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7. The time Poo-poo-palooza came to town.

I had just bought a triplex and was having all kinds of weird unexplainable plumbing problems. The top two units were rented but the bottom unit was empty.

One morning I went over there and found human feces (well I’m not 100% sure it was 100% human, but you get the point) that had seemingly exploded from inside the toilet all over the outside of the toilet and even managed to splatter the walls surrounding the toilet. All I could do was stare.

I didn’t know whether to:

  1. Be impressed
  2. Cry
  3. Call a plumber
  4. Clean it myself
  5. Buy a hazmat suit
  6. All of the above

In the end, I did all of the above (sans hazmat). First and foremost, I WAS impressed! Because what if the tenant upstairs took such a Iarge dump it mystically caused the toilet downstairs to explode? I called several plumbers and they all agreed that exploding feces from a toilet was impossible. And because they all refused to take a look at my situation, I proceeded to cry.

Guess who had to be the one to clean the entire mess up?

Yours truly.

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Via pandawhale.com

Moral of the story? A lot of people say they never forget their first investment property. You better believe I will never forget these stories!

Do you have any crazy stories? Tell us about them here!


Jimmy Moncrief

Adventure-seeker, ice cream connoisseur, real estate investor, banker, real estate author and owner of realestatefinancehq.com.

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If you’re looking to submit an article or partner with us in other ways, please let us know here.