Thank you all for the responses and welcomes so far!
To address a few concerns -- I'm happily married and my husband is a fellow Caribbean-lover that will be going with me, so no, I didn't meet anyone there motivating me. As I said, I've been to numerous places and have had my mind set on a Caribbean relocation for a while (~5 years... comfort in job kept winning over where I'd actually rather be), it was the people that stood out to me in particular at DR. It was an all-inclusive, but I have been to plenty of those, and the treatment in DR was still above and beyond - both in and out of the hotel. Regardless, I am aware that another trip to DR would have to be in the works before relocation. I've already begun collecting the necessary documents to apply for a visa - I know the move itself is not going to happen overnight, which is why I'm starting now.
I'm unsure of what the job situation will look like, which is why I posed the question. Currently, I work 2 days from a home office and 3 days in an actual office (for the same company). I'm considered an in-house designer, and I haven't discussed if the company would be open to allowing me to work entirely remotely yet. Not hugely keen on bringing up the topic until I'm further in the process, as they have a history of letting go of people who express a desire to leave. I definitely appreciate the responses in this regard though, since it sounds like I will need to be dependent on a US income. Does anyone know what I would be looking at as a typical rate for a DR web designer? (For sake of comparison).
My wedding photography thus far has all been freelance (hired directly by couple), and I'd plan to keep it that way. I'm not sure how well that would go down there with existing competition and inclusive packages through resorts, as mentioned by LTSteve.
As far as where I want to live, I'm definitely a beach person. I've read great things about Las Terrenas, just wasn't sure that would be the best spot if I was in need of a job.
For whatever it's worth, I'm to the point that I'd rather live in the Caribbean working at an Ice Cream shop than continue to live comfortably and monotonously in my current lifestyle.
Hi:
Let me start with the last line of your post. Moving to the DR might change your mind set temporarily but coming to live here thinking this is going to solve your problems is not accurate. Yes it will be new and different for a while but then you will find another set of problems to deal with. Working in an ice cream shop at $5 US dollars an hour is not what you want. Living on $5 an hour is impossible unless you want to live in a cement block house with no windowns or doors, no electricity and no running water. Oh yeah, I forgot the part about crime and you being a "gringa" so no one will be overly sympathetic to your situation. DO NOT move to the DR without an income source from North America otherwise suck it up and continue your life as is. Coming to the DR for a couple of weeks at a time and don't stay in all-inclusives. You have not experienced the real "island" life otherwise. Just about everyone dreams of life on a tropical island. You can get there at some point in your life but just remember paradise doesn't come without a price. To live and work in the DR legally you will have to apply for residency. For two people and having an attorney to assist you in the process it will cost you anywhere from $1000-$1500 a person. That is in US dollars. That process starts in your home state where you get the necessary documents and get them to the nearest Domincan Consulate for approval. These documents include, birth certificate, marriage certificate, bank statements, passport copies and a criminal background check done by the state police, which includes digital fingerprinting. It is a complicated process and then you bring all of this to the DR, translated in Spanish and approved by the consulate and turn it over to an attorney to walk you through the next steps. What I am trying to tell you is that there are many hurdles to jump over to get here. In addition, there is a huge learning curve to living in any foreign country. As far as Las Terrenas, this is unlike what you will find in most of the DR. There is a large European population of French, Itlalian and German ex-pats and just about every other European country is also represented here. Las Terrenas has a European flavor but also has a large, spread out town of local Domincan business, along with Haitians who also populate LT. The positives of this is that you have the best of both worlds. You have many services and businesses you may not find in other parts of the DR. The restaurants here are very good. There are many small hotels and only one all-inclusive in the LT area. The bad news is that prices are driven up a little because the Euro is more prevelant than the dollar. Although most things are priced in dollars. Living in Las Terrenas is very interesting. Some of the most beautiful beaches and scenery are found here and on Playa Bonita and Playa Coson. If you are a beach person you will find it wonderful. I would suggest you check out the tourist guide at the top of the Northeast Thread. You can also go to lasterrenaslive.com. I owned a condo in LT for 6 years. Lived in the DR for about half the year and was in the States for the Spring and Summer months. The summers in the DR are very hot and sticky. I have since sold my condo and live back in the States permanently. My priorities changed and my wife and I decided life in the DR was no longer our dream. Take your time and don't be so impatient. Plan and travel here and check it out. Good luck and good travels