I've talked about this kind of thing with friends recently, primarily with regards to cost of living. I and my wife make pretty good wages but feel broke as hell in NYC. It seems like both NYC and SF have become expensive to the point that living here can make you feel poor regardless of how well you do... which puts a dent in quality of life.
How many cities in the country have interesting culture, decent jobs base and aren't too expensive? The short list we keep coming up with seems to be:
Seattle
Portland
Austin
Philadelphia
I'm curious about Boulder and/or Denver. Boston, DC and Chicago are all too expensive. I know nothing about some of the big midwest/southern towns (St Louis, Atlanta, Miami?) so it's hard to say, at least in the states.
Amsterdam is gorgeous, less expensive, and has a great bike culture as well. Wish it was easier to move overseas
Sorry for the moderate derail, urban living just interests me a great deal...