Right now I'm self managing and renting to a family member who is getting a great deal (whole house to themselves) so I eventually need to get it up to market rent to make any decent income.  

Eventually you will receive funds less the 1/3 collection fee from the Attorney forwarded to you."

He will eventually inherit something but hopefully his path is well set by that point and he has no need for the money.Parenting is not always easy.  

Most people resonate with that and I eventually get the listing.  80% of the leads turn into listing eventually. 

I am looking to live here and eventually house hack so as this opportunity already has 2 trailers it seems like a great fit for me. 

The model worked well for about 6 months and so on but went south after the strike and there were lot of cancellations and schedule changes so he eventually decided to terminate his lease.

If you start small you could either get a property manager which cuts into eventual profits, or convince your wife to help out in terms of managing loosely.

I think I would eventually cash flow after a few years with rent price increasing, but not much. 

Is it just based on property appreciation alone and the hopes of mortgage percentages eventually lowering and slowly increasing rents?

If it gets worse, which it could given that the assumed reasons are pollution and global warming, it could eventually wreak havoc on the country's tourism industry, especially Punta Cana.