Was there any communication that the job he'd done was not satisfactory? 

I may not disclose every detail right out of the gate until I evaluate the best way to communicate.

A good start is making sure the attorney communicates in a professional manner and responds to you.

How often they communicate what’s going on as well.

Yes, meanwhile they justify exploitative sales tactics and build backwards work cultures where loyalty is valued over good communication skills, integrity, and merit. 

Property management and cleaning is key - since you don't live far away, you can get away with managing it yourselves (communicating with guests, arranging cleaning, arranging repairs) but you need to find a cleaning service who would be available in the short turnover window.

I can assure based on all my communications with this company and speaking to several people who used them multiple times They are legit

Only a small fraction of human communication is the words themselves, you just loose too much with written word sometimes. 

What i used to do to find services like that was to just find those people on google or google maps and give them a try (https://goo.gl/maps/JhUyEFKVXkH2) unless you can get a good recommendation.Typically, i would go over 2 or 3 different ones to see how well they communicate, how reliable are and how much they charge etc.

I then plan on doing all the communication and marketing of wholesale deals under the CashMoneyDough name to protect myself.