The inverse becomes true as someone's net worth drops as your Risk of Ruin (RoR) flies up exponentially when you're dropping a lot of your bankroll on one wager). 

I'll wager you have come across these folks and seen this in play.  

I've actually been looking at parlaying several of the prominent friendship/contacts I've made on the island into a possible real estate business wholesaling and/or flipping.

For example, if someone built or retrofitted a building in either Bristol into trendy lofts or apartments, I'd wager they would be popular. 

I would easily wager there are more scammers, amateur and professional, in Florida per capita than every other state excepting CA and NY.That still doesn't explain the magnet you have.

You take that money and parlay some of it into the next one, then the next one, so on and so one.  

If I didn't know you or your husband from any Dick, Jane or Mary, and you refused to show a proof of funds or Pre-Approval... and refused go meet with them to ensure safety I would wager its not safe for the agent. 

I'd wager the latter may be costlier. 

This may help dictate what is best suited for you.I personally would try to parlay your skill into the way they can best relate to real estate.For example if one of you were a mortgage lender at a bank I would recommend looking into doing private money lending. 

Only 2 options if you are a W2 wager earner. 1.