@Chip...I really don't fall into the category of your "typical" westerner. I visited Santo Domingo last year and used the bare minimum. I can honestly say it was one of the greatest experiences of my life and I would trade this rushed, confusing lifestyle here in the US for that any day...but I do understand what you're saying. Thanks!
While you may be fluent in Spanish, if you can't pass as a Dominican from the North you will stand out especially in a tourist area such as POP and therefore will be difficult to get decent prices for things as you will be expected to pay more. I would recommend in the beginning you buy at supermarkets with a scanner until you know what costs what. Also, from what I've seen, people that make RD18k a month generally pay no more than RD6k a month so if you could work out a free apartment with them and free schooling for a kid it looks doable. Granted, you will not be more than likely able to go to a private health clinic and the public ones are slow but all the better if you can negotiate a health plan with the school. Furthermore, I would recommend you research prices for costly items like furniture or appliances here on DR1 and be wary of Dominicans taking an interest in helping you get the best prices UNLESS they are (
Good People who) who go to church regularly. Of course the best way to meet these types is to go to church.
Finally, you will need to really stay away from imported foods but buy local goods and be prepared to eats lots of the bandera and vivere. A few sandwiches are in the cards too if you are willing to eat pan de agua and jamon picnic. Suerte.