I have a friend who I learned a little bit about Real estate and jumped right in, buying an empty property that needed rehabbed in a very bad neighborhood and he ended up going bankrupt due to naivety.

So they can not clearly identify if that property and the numbers to that property are a good deal or bad deal.A good deal to me could be a deal that could make you go bankrupt.

It would be a shame to see the OP take a bath or go bankrupt as a result of somebody like me not speaking up.  

They certainly are not making tropical islands any more but PR was in trouble before Maria and is probably in more trouble now (remember before Maria the talk was whether PR would default and go bankrupt and need conservatorship).I would say if you are set on an Airbnb in Rincon, the next step would be to take advantage of the slow market and book your own Airbnb to Rincon and spend some time there to assess.

I've been where you are @Justin Dziedzic thinking that this would be the thing that bankrupts me! 

There are many Title Insurance companies, the majority have been in business for decades (some perhaps a century) --- there is a reason they haven't gone bankrupt and out of business.

iFunding was one of the originals, and it just went bankrupt.  

The breakup of relationships have bankrupted more investors than any other cause. 

Almost went bankrupt and learned a ton. 

Then on one game, he went bankrupt almost immediately because the market cards he drew that night didn't go his way.