Mika,
Thanks for your response. I've been traveling around the country several times a year for the past decade, with trips ranging from a quick weekend to several weeks, but I am not an expat. Chiri, Tambo', Hillbilly, Robert, Criss Colon, Windeguy, dv8, and a number of others are, so I'd try and build an online rapport with them, they give great advice.
The number of beach communities from Costambar-Puerto Plata-Sosua-Cabarete-Rio San Juan-Cabrera make up the "North Coast" or "North Coast Complex." You should think of the Complex as more or less one very large community, as people are constantly going back and forth. There's a lot of variety (Puerto Plata is the third largest town in the country, while Cabarete is almost exclusively geared towards beach surfer tourism.
A lot of people in the North Coast like Sosua, because (once you get away from the sex tourism stuff on Pedro Clisante) it's actually a neat little town that has more or less everything you need. Properties for rent are readily available, and of course the International School is right there. There are other areas of town, but the "real" Sosua community is mainly focused in Los Charamicos about five minutes from the more infamous area.
The adult stuff happens in an area called El Batey, although local authorities and business owners have been pushing to make the trade much more discreet, probably in anticipation of the new cruise line port being built in the Puerto Plata area. I'd steer clear on weekends after 8 p.m., but other than that, it's pretty quiet.
Cabarete has a beautiful beach, but it's a bit rough for young swimmers, and after that, there's not much to do. However, it IS centrally located in the Complex, and has very nice condo properties available. They can be a bit expensive, though.
Cabrera is positively charming, and is quiet and peaceful, but is a ways from the "action." Also, you're an hour from the airport, but if that's not an issue, I'd certainly check it out. Castellamonte is a poster on this site, and runs a business out there, so you should try to get in touch.
In the central valley (Cibao), lies Santiago, my favorite DR city. No beaches, but great spring-like weather year-round. It's the regional capital, so tons of interesting stuff going on at all times. It is NOT geared for tourism, so you would have to work on your Spanish skills. But it's a totally enriching experience, and you'll meet a wide variety of Dominicans. The expats there are more or less fully immersed in the culture, so while you may have challenges attracting people to a school, you'll likely do well with a summer program focusing on expat locals.
Jarabacoa is where well-to-do folks from Santo Domingo go on the weekends. It's very eco-touristy, much like Costa Rica. Slow pace of life, highly affordable, but not much infrastructure compared to the options above. Those who go love it, and it would be ideal to focus some of the activities for your retreat up there.
Las Terrenas probably has the most diverse expat community outside of Santo Domingo and the North Coast. Lots of French and EU folks there, although more NA expats are constantly arriving. It's one of the most beautiful areas on the island IMHO, and has a nice blend of locals, tourists, and expats.