Your biggest pains and challenges as a landlord

[Joe Mahavuthivanij]

I'm a San Francisco-based software guy who rents in the city, but owns/manages some rentals an hour north.  Till now I've kept things decently organized with a combination of Google Docs, coffee, and services like Lovely, Cozy, ApartmentList, etc (I have no affiliate with any of these services), but haven't quite found the perfect "Goldilocks" fit.  I started building and testing a concept, but that was foolishly before talking to other landlords, so I'm designing something new with input from the community.

*I'm not selling, promoting, or pitching anything.*

However, I'm very interested in is hearing about your biggest or unique pains/challenges, what you'd improve, and discussing how it could be fixed.  Basically, it'll help me figure out what to build.  Some features that I like from other services include: online applications and screening, monthly rent payments, and ad posting.

With the community feedback, I hope to build something that makes being a landlord awesome.

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Some of my biggest issues are meeting tenants to get applications back.  Nowadays, I mostly do open houses so I don't have to cross the bridge and sit in traffic to do one-off showings and get applications online.  Also, tracking tenants who rent rooms out on Airbnb is an occasional issue.  What are your challenges?