My wife, Kim, and I currently live in the Caribbean and we're moving back home this fall(2016).

Agents are not raking money hand-over-fist, driving new cars, and jet-setting to their Caribbean vacation home every other month.If you want to read more, this question has been asked thousands of times and you can find lots of answers utilizing the search bar in the upper-right.

I live on an island called GRENADA, located in the Caribbean.

Basically what I'm looking for are the countries that would be the easiest to get started in, I'm not fluent in Spanish but I have basic proficiency and I'm comfortable enough I think with the cultures in the countries I've been to where I'm able to see myself doing this but I have never dealt with anything like this before in terms of investing in a country so I'm a little lost as to how to evaluate one country against another.I've narrowed it down to Mexico, Central America, Caribbean or Colombia.

Get you Appfolio (or whatever system your PM uses) and review it, visit a couple of times a year, and vacation in the Caribbean.  

Mexico and Central America match time zones well with the West Coast, and South America and the Caribbean match up well with the East Coast.3.

Louis but have heard positive things from people who have either lived there or visited.I have a little experience in REI as my husband and I are currently house hacking a 4 plex in Oakland, Ca, and I bought land and built 6 vacation apartments on the Caribbean coast of Costa Rica that I STR. 

We hope to find a wooden concept house that is fit to resist a hurricane on the island of Sint-Eustatius.My name is Ramon Vissers, I’m a real estate developer from Amsterdam and also Active in the Caribbean.

I am a Foreign National based in the Caribbean and I own a multi-family property that needs a little rehab in Cleveland, Ohio.

More specifically, my target area covers Mexico, Central and South America, the Caribbean and Southern Europe.Your question is pretty vague and I could write a 5-page answer on it.