It's something we have been considering a lot lately. Personally, I'm looking for some happy medium. A house in a basically rural environment, but a reasonable (30-60 minutes) commute to a small college town. Currently we have our eyes on Northern Vermont in the vicinity of Burlington.
Being close to a small to medium city with a decent college population generally means there is stuff to do (restaurants, theater, good pubs, movies, etc.). And it takes me 30-45+ minutes to get into Boston and park to do anything now and can be such a pain we frequently pass; and we only live 5 miles from Boston! And if telecommuting and consulting dry up for a while, I could hopefully find at least a moderate salary (for the area) doing some basic IT work in town.
So for now, I'm trying to build up a consulting business, looking for good telecommuting opportunities, and planning for a few years down the road. Maybe it will happen, maybe not. But for now, it's a nice daydream! (go to your happy place Sean ;)