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12 Things I HATE About Landlording

Brandon Turner
6 min read
12 Things I HATE About Landlording

I was cruising around the BiggerPockets Forums several years ago, and I stumbled upon a thread started by Karen M. titled “Tell Me What You Hate About Landlording.”

I thought it was a fascinating discussion—to see what some people consider the worst or best parts about landlording. After all, we landlords tend to get into this “Real estate investing is awesome!” mentality (bloggers, like me, are most guilty of that!) and love to talk about the good stuff. Oftentimes the hard stuff gets ignored, because no one likes a complainer.

Well… I’m going to do some complaining!

It’s my hope that this post can serve dual purposes:

a.) Help others get a realistic vision of what landlording may look like, and
b.) Hopefully generate some incredible discussion in the comments.

Let me preface everything with this: I already know about 20 people are going to put a comment below that says, “This is why I use property management.”

I agree! Many of these problems (not all—but some of them) would not affect a person using a property management service. However, any honest real estate investor who uses property management could easily come up with a list of their own 12 things they hate about investing in real estate.

Arguing property management vs. self management is a topic for another day. The fact is: I am a landlord.

Finally, if you are reading this, I would LOVE if you do me a favor and comment at the bottom of this post, offering me (and everyone else reading) some advice to help overcome some of these issues. Also, let me know what you hate the most about landlording.

I look forward to seeing what you have to say!

Without further suspense, here we go.

Frustrated student behind the desk keeping hands on face

12 Things That I Absolutely HATE About Landlording

1.) Never Truly Taking a Break

When I managed my own properties, although I set specific office hours, didn’t answer the phone in the evenings or weekends, hired others to do most of the labor, I still never got a true break. Even if I got a physical break, my mind never stopped working on the landlording business.

I still carried the stress and the knowledge that things might be going wrong at any given moment. Once I even took a cruise through the Caribbean—no cell phone, no computer, nothing. However, I still thought of, planned, schemed, read, and discussed real estate investing the entire the trip.

Sometimes… it’s nice to simply ignore it all.

2.) Being Lied To

“I mailed the check last week!”
“I don’t have a dog! You must have just seen my nephew in the window.”
“I called twice this week and no one answered, so I just let the roof leak destroy the property.”

Ugh. I hate lying tenants… but when I was managing my units, I couldn’t seem to escape it. Even when I caught them in their lie… they continued to lie to try and cover up the previous lie. It was a never-ending battle!

3.) Dealing with Contractors

This is just the worst. Trying to find reputable contractors that doesn’t demand your first-born child is… tough. However, even more than just the money, it’s the dependability.

Even the expensive contractors sometimes failed to show up when they were supposed to, failed to bill the correct amount, failed to answer their phone when there was truly an emergency. Sometimes I felt like I was going through contractors more often than I was changing my socks.

4.) Water Leaks

Once, I had four major water leaks in a six-month timeframe, each causing several thousand dollars worth of repairs. The fact is, water is a battle that every real estate investor will face with any property they buy. But it’s especially bad for landlords with older properties.

Whether it’s a roof leak or a plumbing leak, water is the enemy. For those of you battling the same thing, be sure to check out Darren Sager’s great article “The 4 Things to Check When Water-Proofing Your Potential Investment Property.”

Beautiful woman with pots and buckets dealing with water damage in living room

5.) Watching Slow Motion Train Wrecks

As a landlord, I got a pretty good idea of how someone was living, how they acted, and what their past looked like (from my in-depth tenant screening process). Sometimes, it was tough to watch and not be able to do anything about it. I thought of it as a “slow motion train wreck.”

I could see drugs tearing their life apart, selfishness tearing their kids apart, uncleanliness tearing their health apart. All I could do was kick them out… I couldn’t really get involved in their personal lives.

But I wanted to sit them down and make them read every one of these books. I wanted to teach them how to clean, how to raise their kids, how to respect their neighbors. But I couldn’t—I was just the landlord, not their dad. All I could do was watch the slow motion train wreck, and try to avoid getting hit.

6.) Insurance

Oh, the bane of my existence. I would estimate my wife and I used to spend 20 hours a month on insurance alone. There was always a policy being canceled, changed, renewed, increased, or added for no real apparent reason.

At one point, we even doubled the fun by working through an onslaught of changing laws and policies regarding flood insurance. Properties that were once free of the need for flood insurance suddenly needed it. Other policies were requiring us to obtain an “elevation certificate”—for $600—just to keep the current flood insurance we already had.

My wife was spending more time talking with our insurance agent than her own mother. Such a great use of time.

7.) Being the Bad Guy

Sometimes I just got tired of being “the bad guy” in every situation. For example, we had a small water leak (yep, again) on day in a top-floor unit from a drip in a water supply line in the attic. We sent a contractor over immediately to fix it.

The tenant called a few days later—livid—to chew us out for the leak. To them, it was as if I climbed into their attic and cut the water line just to be a jerk.

Seriously, people.

8.) Paperwork

The more properties you accumulate, the more paperwork it takes to manage and control them. From closing documents, insurance documents, mortgage documents, tenant files, leases, applications, and taxes—the paperwork can really pile up.

Even the most organized landlords out there still have to deal with mountains of paperwork and office work just to own their properties. Yes, it might be only 10 minutes here, 10 minutes there… but it adds up.

9.) Babysitting

I often used to think of landlording as babysitting. Let a tenant do whatever they want, and they would quickly become their own worst enemy and destroy the property, turning it into the town dump.

two young men sitting back to back with arms folded in frustration in a living room setting

As a result, landlords have to consistently monitor the tenants to make sure they are “behaving.” I can remember sending letters or calling tenants about:

  • Throwing garbage over their apartment decks
  • Piling trash bags on their apartment decks
  • Parking on the lawn rather than in the parking lot
  • Not throwing garbage in the woods because the dumpster “was too far away”
  • And a lot more that I was never even made aware of because my wife was so amazing at trying to shelter me from it all!

I just wanted them to treat the property the way I treated my own house. However, I knew that was never happening.

10.) Refinances

Trying to refinance rental properties is such a pain. It seems every day there is a new form that needs to be filled out, a new document that needs fetching, a new law to work around.

Obviously I’ve always understood the need for the laws and the rules and the rigidity… but it’s seriously enough to drive a person crazy.

11.) The Aftermath of an Eviction

gw throwing tv out windowTo be honest, I never minded evictions that much. I’ve always tried to screen tenants well, so it was never a big concern.

When I have had to do an eviction, it was usually pretty quick and painless once my lawyer took over.

However, it was the aftermath that I hated. The junk they’d leave behind, the filth on the floors, walls, ceilings—everywhere.

12.) CapEx

Finally, let’s talk about CapEx. CapEx, or a capital expenditure, is a non-regular expense that needs to be replaced only once in a while. This could be replacing the roof, replacing the furnace, replacing the driveway or parking lot, replacing all the windows, etc.

Let’s be honest… our properties are falling apart every minute of every day. Every year the plumbing gets older, the roof shingles get a little thinner, the asphalt a little more cracked. This stuff may seem like it’s not a big deal, but the fact is: there is ALWAYS something new to fix and replace on a property. There is no “done.”

This is why it’s so important to budget for CapEx when analyzing a rental property, and why we make it an important part of the BiggerPockets Rental Property Calculator. Ignoring CapEx is a quick way to lose your expected cash flow.


I know this post sounded like I was whining, because… well, I was. However, landlord is still awesome because of all the great things it can do, like helping people secure a place to live while also providing cash flow for property owners.

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Now, it’s your turn. What do you hate about landlording?

Let me know in the comments below!

Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.