As a lender, every FSBO I've done has been quite painful.

It is a 100% pain to get a loan self employed3) Would not be an issues.

It's a pain but the post office has a sytem set up for it.I told the tenant I couldn't do anything for him until AFTER Memorial Day and after that I would figure out if we had a spare and get back to him, , but I told him to in the meantime, call the post office, hold the mail, and manually pick it up, and keep looking for the key.

There is aircover which essentially is guest damage insurance but it's an absolute pain to deal with and get money out of Airbnb.

But a pain on the back end.

Try to take the emotions out of it (even if she is a pain in the butt). 

There are programs like Avail and Stessa that do this and aren't too expensive. 3) It's tempting to just use a spreadsheet when you have one property but before you know it you have several and it's a pain to switch over to an actual system.

. 🏡🏢 Rather than tell you what features I want to build, I would love to hear from more investors like you about what challenges you’re facing, what’s not a pain point and what tools you have that are useful, what tools aren’t — so that I can build something would actually be helpful to you!

I can definitely say that while the bigger fire we had was a pain... it actually worked out really well... in the end we had a much improved property, and we stepped in and did as much of the work we could do ourselves that the insurance company was compensating us at  'retail' rates for... like painting, and replacing cabinets, and other simple tasks.  

I understand the net profit amount would be higher if we continue to leverage and scale, but there is something to not having a mortgage on half or all of our portfolio that interests me from a psychological standpoint.