There are certainly some people who are doing it well, with 200+ units 'automated' as they claim, but I truly don't know what payoff they're getting, or how handsoff it is.

We haven’t ever filed any insurance claims.

I don’t expect to file insurance claim and it's probably an act of God clause or whatever it’s called these days. 

He claimed he didn't even notice it and it must have already been like that.

Or do I pursue suing him for twice or triple the amount of the deposit in small claims court?

I should clarify that I initially bought the house as a primary residence and that I've never claimed in my taxes as a rental property.

One person is sending me screenshots of multiple apps that list money paid to her from 3 different jobs and claims to make $48,000 per year but the 4 months of pay she showed me add up to around $22,000.

One tenant in Chicago area claimed there are ants in the apartment. 

I then called the insurance company to get it expedited whom said they do not inspect properties without a claim being filed and they do not inspect properties on behalf of mortgage companies either.

It's those maniacs that buy homes cash via quit claim deed off of craigslist that really get screwed.Make sure your property manager is a licensed real estate brokerage.Google Clayton Morris and/or Morris Invest for a cautionary tale of what not to do when buying turnkey real estateUnderstand you can not eliminate all risk, only mitigate it.