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!

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.

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.

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?

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