Did you self manage or use a Property Management Company? 

His bank was in a state like Indiana, while one of his companies is in Wyoming, and just all sorts of weird sketchy stuff that accumulated over the period working with him.

I've considered a property management company, but the cost just doesn't seem worth it although it would be convenient.

We own and operate a mid size REI and property management company in Marquette Co. (~300 units or so). 

Quote from @Andres Lasaga: I am in the process of selling a property to the tenant I have been renting the house for 4 years.I want to outsource the promissory note collections and reportsIt would be only ONE property, for now, any recommendation of a company that can manage the collections and reporting?

I'm an investor and property manager company owner. 

If they think they have an "Airbnb" Unless they own the publicly traded company, then they only have a STR, or a vacation rental if they have a nice place/location.

I currently pay a premium price for my turnovers for a local cleaning company that specializes in STRs.

He is not trustworthy and i would stay far away from that company. 

Scumbag company.