Josh, I stopped working in around 2002 when I was selling everything I was not going to bring to the DR. That was the last time I had a day job for a company.That's one key thing right there in my opinion. You chose to live there, even if not considering it a privilege. Many people have to for example live close to where they work etc., usually in their home country. I'm not saying there's something wrong living in your home country, but for many people in particular the warmer climate does constitute as a privilege. For me it does.
I believe I have read on this forum that you have also worked in the DR (as in a company physically in the DR). As the DR is a country of quite a bit fewer opportunities, this is also usually not that straight forward for just anyone to get a job that is any good in the DR. I did in fact work in a company that was a DR company, but it was just half-good as while my salary was nowhere near a normal salary in the DR, I still was not happy with that. So after getting out of that employment, I have considered myself to be privileged in the sense that I have been able to have an employment that has given us a salary the same level as in my home country (more or less), while still being able to enjoy the positive sides of what the DR has to offer.
I know many other posters on this forum also physically work in the DR, and they all have my full respect as I can imagine that working or even running a business in the DR might not be that straight forward as back home.
Music was always a hobby for me in the USA (from the age of 15 I was playing a gig here and there from time to time). I also play gigs here on occasion.
But no, I never worked full or part time in any company business in the DR. I am happy to be retired in that way and just play some music when I can.
Enjoying my hobby is much harder to do now since there are so many wandering minstrels that come with a guitar and play illegally in the local bars and restaurants. They don't consider getting paid for a gig "work"... Yeah, it is working illegally unless they are legal residents. (I just watched the latest movie on the Beatles and they had a sub story about two guitar players from the USA that wanted to play a gig where the Beatles played - They did play, they were caught and they were deported. ) Here in the DR, it does not matter if you enter on a tourist card, you can work and drive as long as you want to without residency.
I came here from 10 years of living in California. I assure you the climate there was MUCH better than it is here. I do miss that weather, so the weather here is no privilege over California. The DR is a place to come to and retire to, not work for a pittance.