What’s the biggest problem you deal with as a landlord?

Question

Hey everyone, I’m curious what problems rental owners are running into right now, big or small.

What’s the one thing that’s the most frustrating, takes way too much time, or just doesn’t have a good solution yet?

Could be tenants, repairs, rent collection, paperwork, taxes, anything. Would love to hear what you’re dealing with. Thanks!

Daniel Jung · Answer

For me it is keeping track of what was said, to whom, and when. A tenant texts about a repair, emails about parking, then calls about a lease question, and each answer lives somewhere different. Nothing is hard on its own, but when something is later disputed, you are digging through three places trying to rebuild one conversation. What fixed most of it was boring: one channel for everything, and every request, promise, and deadline written down in the same place for that unit. If a call happens, I send a short follow-up message confirming what we agreed. It feels slow in the moment, and it saves hours later. Most landlord stress in my experience is not the work itself. It is proving later what the work was.

Matthew Morrow · Answer

@Matteo Scali me again! Turnovers, hands down. Not the turnover itself, it's managing contractors and making sure the work actually gets done right, especially when you're not there. One month vacant can wipe out a year of cash flow, so speed matters. Leo's photo idea is a good one. We lean on before, during, and after photos for every job.

Divin Kanyama · Answer

@Matteo Scali For me, the biggest frustration is coordinating repairs—especially smaller jobs that are urgent to the tenant but not large enough to attract a reliable contractor. The repair itself may be simple, but scheduling, access, communication, estimates, follow-up, and verifying completion can consume far more time than expected.

There are plenty of maintenance platforms, but none fully solves the local “last mile”: finding dependable vendors who respond quickly, charge fairly, and document the work. A solution that combined trusted local contractors, transparent pricing, scheduling, tenant communication, and completion photos in one place would be genuinely valuable.

Richard (Ryszard) Cieplechowicz · Answer

Small repairs that sit. A slow drain or a loose handrail gets reported late, and by the time it is a real repair it costs a lot more and the tenant is annoyed.

A short walkthrough with photos once or twice a year, plus an easy way for tenants to report things, catches most of it before it turns into a bigger bill.

Leo Stein · Answer

For me it's usually the small stuff that eats the most time: maintenance requests that arrive with no photos or details, so it takes three back-and-forths just to know what's wrong. Asking tenants to send a photo and a short description up front, plus a quick note on when they're home, cuts that way down. Curious what others have found that works.

Matteo Scali · Answer

Thanks Daniel, that’s a really interesting way to put it. Having every request, promise, and deadline written down in one place for each unit makes a lot of sense, especially when something gets disputed later. Sending a follow-up after every call is a smart habit. What do you use to keep all of that in one place right now?

Matteo Scali · Answer

Thanks Richard, great point about catching small issues before they grow. A walkthrough with photos once or twice a year is a smart habit. Getting tenants to speak up early seems like the key. What do you think would be the easiest way for tenants to report things, like a quick form, a text, or something else?

Matteo Scali · Answer

Thanks for coming back, Matthew! Using before, during, and after photos on every job is a smart way to keep contractors accountable when you can’t be there. Speed clearly matters a lot on turnovers. What do you think would help yours move faster, better contractor scheduling, quicker updates, or something else?

Matteo Scali · Answer

Thanks Divin, really thoughtful answer. Having trusted local contractors, clear pricing, scheduling, tenant updates, and completion photos all in one place sounds like it would solve a lot. Small repairs seem to cause more headaches than they should. What do you use to manage repairs right now, and what would it be worth to you if one tool handled all of that?

Matteo Scali · Answer

Thanks Leo, that’s really interesting. I wouldn’t have guessed that the small stuff takes up the most time. Roughly how much of your week goes to back-and-forth like that, and what would do to make that part easier for you?

What’s the biggest problem you deal with as a landlord?

What’s the biggest problem you deal with as a landlord?

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