I already have proof of concept in Raleigh as Ive talked to multiple people (including the agent Im working with there) saying airbnb-ing rooms is a cash cow there. 

I know it may sound common sense, but people do struggle with understanding that water follows gravity.

Lots of other people had bad experiences. 

.: Since you're in Wyoming isn't setting up a Wyoming Trust a lot easier than for us out of state people? 

did you know that banks have their own font and font size (so its like creating your own currency, if you do it and use the right people you will know). 

The founder appears to have been involved in businesses outside of real estate: ‘My dream is a locally made grooming products business’ | People | nashvillepost.comSo it does not appear there is a lot of track record there, but those are questions I would ask.

Multiple people including myself have tried to caution him of the the true costs but he's been repeatedly dismissive and has made it clear we give him motivation and he wants to prove us all wrong (whatever that means). 

welcome. it can be profitable but do your due diligence. network with people that are doing it and try to see if can find mentor.

My immediate area, 5200 people, has 3 outdoor self storage and 1 new climate controlled.

I warn people over and over and over to know what they are buying and to go personally see what they are buying.