A lot of insurance companies do like the co-living model.

And when the company you're suing has shut down and apparently has no money, is it even worth the effort?

The companies that market themselves as "garage door companies" (residential) also almost always do commercial stuff as well, such as what you are looking at.

Quote from @Elias Halvorson: Aloha Diandre, You will get 100 people responding on here responding they can do it and their company focuses on it.

I'm a local investor, flipper, and property management company owner.  

We learn to build relationships with people and companies.

His lawyer even told our lawyer he had a crappy case.I was a bit annoyed that our insurance company settled for a $70K payout. 

Prosper and Lending Club also offer peer 2 peer loans, usually up to $40-$50k depending on which company you look at.

This was my first investment property and I had a poor inspector who missed all the electrical and even though the roof had about 5 years left my insurance company made me do that.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.