Interesting question.
My first visit to the DR was in (I think, my memory may fail me) 1987. I went three times, staying in the old El Mirador high in the hills overlooking Sosua. My motive then was partying. It was a different DR, and certainly a different Sosua back then. Heck, El Mirador is gone...
I've traveled to the DR prolly 30 times the last 3 years, for a week-10 days at a time, traveling the country often and being with Alida and her family in Santiago, and bringing my mother and other friends down with me. I begin to miss the DR before I leave each time.
My perspective on the world and my place in it has changed, morphed really, over the years. I have gravitated away from materialism and toward relationships and people. I no longer have a need to change the world or people. I'll just accept them.
I've pondered moving to the DR for a while, knowing I have family in the U.S. I can visit when I want. I see a greater degree of individual freedom and liberty in the DR, as long as you render unto Caesar what he claims. There is little, if any, Nanny State. One must provide for themselves, and know this at a very early age. I enjoy the incredible raw and diverse physical beauty of the country, like a continent unto itself. I enjoy being immersed in the culture. I don't have a problem with the lack of First World conveniences, but know they can be found if you need them.
I look forward to a more simple life. I've been involved in some very complex entrepreneural businesses in my life, and done OK with them. Been there, done that, etc. My recent "detoyification" program has been enjoyable, to my surprise. I'm not going to miss the attention "toys" require, and feel no need at all to replicate them in the DR. I want the simple peace that comes from understanding how important family and friends are, in an environment that nurtues that...and the Dominican culture certainly does that. I'll just have to deal with Grahame, Chip and Hillblly humiliating me on the golf course. I guess you can't have it all...
Additionally, we're planning a business that combines a personal passion with opportunity, based in the DR. We'll see how that goes.