As somebody who has lived in San Francisco for going on a decade, there is something pretty damn alluring about the mountain lifestyle.
I just got back from a few days in Telluride. I was lucky enough to be staying in a slopside condo with 3 Denverites and a born and bred Montrosian. To top it off we got the locals treatment thanks to a couple of Telluride friends (a housekeeper/skier and a lawyer/skier). There was something really great about going into the bars and restaurants and having everybody know the people who were our "guides." It was like Cheers in the mountains.
The only thing I did wonder was what all these locals did for jobs and how they made ends meet to pay for the rent in T-Ride, which I hear is atrocious (I was told that many of the laborers and kids working at the resort are bused in from Montrose where housing is way cheaper).
The lawyer we were hanging with seemed to know everybody in town. I met some of the firemen and folks who worked as bartenders and waitresses. Everybody seemed to love tying a serious one on (then again it was Friday and Saturday...I'd have to hang out mid-week to see what that's like). The appeal of skiing and getting drunk with friends 7 days a week is still there, though not as strong as it might have been in my immediate post-collegiate days. But I hear ya on the "culture" angle. While I don't go to the opera or symphony or theater that much, it's nice to have it nearby. If you were to live in T-Ride, you'd be 6 hours drive from Denver.
On the other hand, it was kind of nice to get away from the tabloid fascinated, reality TV infatuated, hustle and bustle of the city for a few days and just take in the cold air, crusty slopes, and suck down a few suds with some friends. Dunno if I could do it 24/7, but it's damn inticing.
Anyway, my feelings on the subject boil down to this: if you have to ask, then it prolly ain't for you!
And I think it would be WAY easier to do solo than with a family (wife and kids) in tow. If you're solo you can find roommates, live on the cheap, and pack up and move with ease if you decide you don't like it. If you've got a family, that's a whole other ballgame chappie!