Many people have had bad terrible experiences in the past, and with the direction Airbnb is going I don't think its a great idea to rely on them. 

There are a number of property management specific companies that help people hire these employees.

I would recommend listing it on paperstac as well and see what people will offer. some important questions will be is it perfomring?

I'd be worried if people were coming to the home for his business, but if he's simply using the address (same as a PO Box, though to me that would send up a red flag for a business to have a Box #) I wouldn't worry about it.

We decided to contact a few key people who expressed interest in the past to potentially invest on this deal with us.

TONS of people don't follow that rule and have done very well, but I wouldn't recommend it for your first property.I live in Chicago but don't invest here for the most part.

I’m sure a lot of people heard about Sub To financing.

Propstream tends to be the one most people use but Dealmachine has some amazing data that propstream doesn't. 

That describes many people in education. 

If not, I've heard many people recommend a contractor or possible cash buyer.