Will, I loved the book The Richest Man in Babylon.

Every deal is going to be different, and every different exit strategy is going to have its unique set of factors that you'll want to investigate, analyze and be aware of.Pick up a good real estate development text book, take some university-level real estate courses and find someone doing what you want to do and see if you can get them to spend some time with you.

If you haven't already done so - listen to some podcasts and read some books on real estate/business.

As I’m taking a break from reading a book on how to find great deals, I stumbled on to something that looks like it might be a deal.

Is there anyway he can get away with doing that or is it considered fraud since it may not be primary residence if the place gets booked up and he stays at his apartment while booked.

We found one good one and now he's always booked months in advance. 

Out of those categories, what books do you guys recommend?? 

Have  for, who puts up the money, how much, who does what work, who does work you didn't think about, who does the books, what happens if you need more money than you thought? 

I do know that vrbo does offer pay by the booking, but they charge 8% of the booking versus Airbnb's 3%. 

I would also listen to the podcasts and read the BP books to help you get a better understanding and help build your processes.Let me know if I can help!