I grew up in some of the "best" places in the country - Jackson, WY and the Bay Area. I went on to live in progressive, liberal, cool cities - Seattle and Austin - and I have to say that I love St. Louis. Sometimes I think folks who grew up here just can't see it. Its wonderful, and it has so much potential.
There are downsides. There are upsides. We live in a great part of the city. I honestly think I would go crazy outside of the city, but thats me. The outer subburbs do seem pretty generic and stunningly conservative to me. But there are some great inner-ring suburbs with a real sense of community....... the grass is always greener I guess, but what St. Louis lacks in progresive/yuppie-ness it makes up for that with REAL community, diversity, history, architecture, parks, and awesome free stuff to do with the kids. The crime is not a big deal, truly.
There are lots of progressive types here, and much more friendliness ime because beggers can't be choosers
eta: the smoking does suck. we haven't been to a bar in ages..... but there is a strong movement to ban smoking, so you could always get involved with that