Quote from @Aaron Letzeiser: REVISED CODE@Aaron LetzeiserI was hoping to work with Obie, but on the last page before signing the documents, I came across this disclaimer, which made me rethink my decision. 

I do not need information about how to do it.

Educate yourself, become expert, then make decisions from a place of expertise.  

Mediation is a process in which the parties meet with an impartial person who helps to resolve the dispute informally and confidentially.

The tourism authority has had some good information in the past about how many visitors come to each island and, of those visitors, how many book STRs.

If you read Brian's informative book, you will learn that he finds integrity to be #1.

It sounds like you don't have enough information due to conflicting reports.

BP is the right place to start to get both information and connections. 

Do number, size, or area of investments owned play the biggest role in that decision? 

I am hoping to learn more about how investors analyze their deals and make decisions, as well as looking to better understand general real estate investing.