Maggie
Here's my advice for what it's worth. You mentioned you have been to the DR about 5 times. Have you ever stayed by yourself outside of an AI? I only visited twice for about 30 days traveling solo before buying an apartment near the beach in Bavaro. It's a great area and I enjoy my stays immensely. However, I still maintain my home base @ PCB, FL. My plan is to stay 4 -5 months for the next few years and see if I can live with the total adjustment before deciding to stay longer each year.
There have been numerous good posts with excellent advice to reality of living in the DR. Just give it some serious thought on a permanant move. It will be a life-altering event, and you want it to be a good one. If you have already made up you mind then come on down and have a good time. I have met some great people (both ex-pats and locals) during my visits.
As one person prviously posted, I would also recommend that you practice your Spanish (if not already proficient). Plenty of people speak English and other languages, but knowing Spanish will make it easier for you to transition. The area I live in is generally safe, and I have walked the neighborhood numerous times at dark. Just use common sense. Also, there are quite a few Canadians who live in close vicinity of the development where I have bought an apartment.
Best of luck in your ventures. Don