Vacation properties in the Caribbean.

[Joel Brown]

I think it would be awesome to buy a rental in the Caribbean. Someplace that I could visit at times and spend a month or so in the winter when Idaho has a foot of snow.  I could see purchasing a place with 3 or 4 units and the ability to have a couple long term tenants and a couple shorter term tenants. Maybe even rent it on VRBO or airbnb.  I'd have to have some local contacts to clean and help manage and be the "boots on the ground". It would be awesome to get a fixer-upper and spend a month working on it with my son.  Anyone with experience on a specific island or  words of wisdom?  All I need is something that could cash flow and not be a money pit.  I'm not necessarily looking for appreciation as much as gaining equity through rent, and having a place to visit a couple time a year. Cash flow would be a nice bonus. Right now I own a couple rental condos, a business building, and a grade a single family all cash flowing.