Lots of questions

Been trying to absorb all the interweb information I can on moving to the Caribbean. Wanted to bring my custom built fiberglass v8 Jeep, Harley & trailer full of my contractor tools.  I'm understanding I may be facing a LOT of obstacles. Type of vehicles, corruption and extortion being the biggest.  Would it be better to sell it all and buy new equipment there? Is there a Home Depot or Lowe's?  Wife and I been flipping house past 6 yrs. will I be able to find work doing maintenance or improvements in the expat communities? I'm licensed and certified in Mass. in all phases of construction also have a keen eye for design.
Wife is a gym rat, in great shape and considering an instructors cert of some kind, are there gringo gyms there she can instruct expats getting in shape?  she also has a cleaning company as well. But not really seeing much coming from that with the cheap local maids to be had. Were considering the USVI, cost of living is a concern, Roatan, ability to earn is a concern, as is Costa Rica or Belize. But really have never been there. We've traveled extensively in PR, USVI & Mexico. Done with the drama here in the states, time to semi retire, enjoy what we've earned, but not quite ready for full retirement. Any advice is appreciated. TIA.

You have worked it out that DR is a cheaper and perhaps safer destination to settle in the Caribbean compared with USVI and PR. It is much cheaper than most other islands with the exception of Jamaica and Haiti.

To be effective operating your own businesses here you will need to be proficient in Spanish and have good advice. There are expats operating as contractors serving expats in resort areas. It is a different approach though.

Residency appears a must. Get it and you can import possessions with import tax waivers for a limited time. Can you qualify under the investor route? Residency allows you to work and importantly to get a DR driving license amonst other benefits.

My suspicion is that gyms don't make money here. The brand names in the cities may do.

First welcome to the forums.  Have you even visited here?  There is a lot to learn here.

First you will need residency to live and work here.  You will need to qualify for residency.

Then with residency you can bring household items and a vehicle but there are restrictions.  A motorcycle will be fully taxed when you bring it in.

We don't have home depot or Lowes but we have hardware stores. 

For work you are competing with low priced local help.  Your qualifications won't matter much except to expats.  Gringo gyms - we have gyms for everyone.. In terms of instructors exams - not sure but not likely.

I understand wanting to leave the drama.  You will need to visit to see if this country is for you. Yes, the cost of living is reasonable here.

As planner indicated you really want to visit first and get some idea for the type of area you want to settle in, if it is possible to run a business, or if you want to do it at all.  A large percentage of expats return to their home country, the biggest risk being culture. The culture is vastly different in RD and it simply drives some folks crazy  :0|

I don't believe you can import any vehicle with more than a 6 cylinder engine, and it must be less then 5 years old. Unfortunate since older vehicles are easier to maintain and such.

That is a point we rarely discuss .... When referring to expats who move here full time, a large percentage leave before 2 years has passed.

This culture is not for everyone!

I totally agree about the cars.  The older ones have a longer life span due to being simpler to fix.  And not requiring fixing in as many areas, such as non-essential electronic systems.  In my line of work, I see the same thing in elevators.  Very old units, meant to last 25 years, are running well after 50.  New technology meant to last 10 - 15 years, aren't lasting to 10 - 15 years.