"Just a little damage" Walks flat, needs roof and cosmetics. 

If something pops up in the first two weeks, then I will cover it just in case we made a mistake and as an offer of good will.The stray cats are not your fault or responsibility.

Guests normally don't like to be asked to cover damages that they caused and sometimes give a lower rating because we ask them to cover it even though they have COI that insures my listing.So I'm exploring the event guest screening option that they could put down the security deposit as well. 1.

Rail roads he has got that covered. 

My wife and I would remain renting in our current apartment and we could easily afford to cover the mortgage indefinitely if/when it would be vacant. 

Brick v.s siding and covered v.s no converted parking also make a large difference and are items that have to be adjusted for. 

It is always better to start with a multi-unit 2+ so that if something goes wrong, you still have one tenant to cover necessary expenses (mort, taxes, insur, etc).Also, major renovations are not a great idea for starting out as others said, especially out of state.

What is your roof goes, a heating unit.... you're credit card debt could build up quick as a result of this putting yourself in a bad situation.

Not sure if that will be helpful.You could also work with your agent about a big umbrella policy to cover the uninsured parts.

Long-term investment should cover income shortfalls and consider alternative markets outside San Francisco or affordable markets like Texas, Ohio, or Arizona.