I need the ins and outs of preparing to move to the Caribbean.

Try Florida (the state). I know someone considering going there from Rincón PR b ease it's cheaper.

Hi Rookie.

Although most people live at a lower cost of living in PR than in the States, the cost for the same standard of living is comparable if not higher. That being said, the cost of living is still low compared to many parts of the U.S. Maybe tell us more about your specific situation. For instance, if you are living in Southern California on a pension or other fixed, reliable income, and could afford to buy your home (real estate prices on the island are at a low due to the economic situation), then you might find PR to be very affordable.

Why do you want to move to the Caribbean?

Low-cost + Caribbean do not go together I'm afraid.

I currently live in Atlanta, GA and am a Computer Engineer looking for early retirement (49). Just looking to start the second portion of my life and would like for it to be in the Caribbean. If I must I will purchase a house / villa outright (100k - 150k), however I would (like anyone else) more bang for the buck. Everyone's input has been appreciated and need more clarity on if the transition is possible for the tranquil lifestyle. The question was raised why the Caribbean? I have been here for all my life beside the 8 years in the military and would like something different. Visiting the islands from Jamaica to Bonaire, St. Lucia to Trinidad. I visited many, however the my heart isn't set on anyone particular site...just tired if working 60+hrs a week. Who cares about a decent salary if you can't live life.
Just trying to find the best, most cost efficient, and safe area to live.

Thanks in advance Rookie.

Visit.  Stay a while.  Vacationing is not the same as living somewhere.  Your list of 'must haves' is not the same as mine, or anybody else.  What might be quaint while your on vacation may end up being a royal pain if it is part of your everyday life. Start thinking of what you would dearly miss.  I moved to Puerto Rico after living here part-time, but decided that I wanted to live in a different part of the island where there were more amenities.  Is it paradise? No.  Is it pretty darn good? Yes.
I 'retired' in my mid-fifties and glad I did.  My advice is to be the Project Manager of your own life.  A goal is a dream with a deadline attached to it. And after those platitudes and planning , don't get stuck in the zone of indecision: just do it!

Lots of good advice here.  Welcome QBert.  Definitely need to visit and spend some time.  Here is a thread where people have described some costs of living.  https://www.expat.com/forum/viewtopic.php?id=439052

Living in Puerto Rico does offer options to live on different  scales just as it has micro climates. Living in expat communities with the amenities of the mainland has its price as was mentioned being equal to the mainland. Living outside of the expat community can offer more less costly options.For example, I live in a custom created reality based on Puerto Rican historical customs embracing and adapting as much as possible and benefiting from the mainland  infrastructure. I am definitely in the minority across the board but what was created and what I benefit from is more than half the cost of living on the mainland and what I have here would not even be possible due to climate, terrain and historical architecture. Since the lifestyle I have created and the combination involved is not likely to be reproduced easily it is still possible. It all depends on your priorities. Here is a little taste of what can be possible. A 12 room 100 year old colonial mansion with no property taxes under $200,000 that pays for itself with one room on airbnb. A 32 acre mountain top farm with Caribbean views 15 minutes from the house producing fruits, vegetables, herbs and spices all organic with loads of income producing potential with taxes at $84.00 a year. I have been doing all this part-time as most of my business was based on the mainland. Now with internet sales and the new tax incentives I will move here full time to take my emerging life on this island to the next level. If you are creative at all and can think and operate out of fixed idea of what you are trying to get away from the opportunities can be very expansive with what is available. If sipping margaritas on a beautiful beach with fresh ocean breezes caressing your face is what you desire the options are more limited and most likely you will have to pay a lot for that along with the limitations of what it eventually offers. This is just anther perspective of life on a tropical island.

Dear rookie , I'm in the same relative situation and am preparing to move to Luquillo PR . I am from New York where it is highest cost of living in the country and the worst state in the nation to retire economically. PR although some things being the same or higher in cost still is a great choice to live with taxes and insurance alone being considerably lower. Add on the beautiful weather and beaches it's a no brainer. There are different health insurance options you can explore in PR there is a provider called Triple S . I am currently looking into CignaGlobal as it will provide care international . The Caribbean is an excellent choice good luck!

Sounds awesome. Thanks for all the info. Have you heard anything about Honduras?

No I haven't

For better or worse, try not to take you $$  of US territory.... People move to Costa Rica and Mexico for cheap and  you can get a great deal in the DR but DON"T leave the property if you value your life!! 
PR has many options, is relatively safe ( as safe as many parts of NYC if not safer!)  has a lot of cultural opportunities, beautiful beaches and mountains ( you don't have that in FLA.) AND it's USA!!!