Asheville
- The good:
It's gorgeous. Really. One of the most beautiful places in the country.
The art and music scene here will not compare to a New York or a San Francisco, but compared to other half a million person small cities Asheville punches waaaay over its weight class. Its art and music scene is better than many medium sized (2-4 million) cities. There are lots of festivals too, like this: http://mountainoasisfestival.com
The food here is incredible. It's easily as good or better than the food you will find in Boston and New York. It is difficult to find a bad restaurant downtown.
There is, of course, tons of beautiful outdoors stuff to do: hiking, biking, kayaking, backpacking, mountain climbing, just about anything except skiing (it's the South, no snow). There's lakes not far away too, including some that permit power boating. So there is that kind of skiing.
Weather is nice. It can get a little cold/snowy in the winter. Hard winters are not unknown but are rare. Last winter was very mild. Summers are warm but since it's up in the mountains you do not get the soul crushing Southern heat you get in, say, Atlanta or Orlando.
If you are a single heterosexual man... well... you will probably like it. I'm not so it doesn't matter to me, but if I were I would not have been disappointed.
If you're gay, I know there's a decent gay scene. I'm not so I can't talk about that from first hand experience. It's also generally a pretty tolerant place.
Finally, downtown is alive. Unlike most interior cities, Asheville revolves around its center. There are lots of people walking around and lots of people (including me) live right in the middle of the city.
- The bad:
It's a small town. It can feel small after a while.
The tech scene is so-so. There are a few decent startups and a few major employers, but keep in mind this is a small city. If you're looking for a hot tech scene you'll be disappointed. Personally I kinda wanted a break from that, so I didn't care. I found a good job and picked up some very interesting freelance work. If I turn down the Silicon Valley offer I may go more in a freelance direction, and try to bootstrap my own startup project too.
Asheville is an island amid the pentecostal / fundamentalist Christian back country of Appalachia. Drive for 30 minutes in any direction and you are in the hiiieeeeells.
The job market frankly sucks for most people. If you're in tech -- and especially if you can freelance/telecommute -- you can escape it to some extent. But the joke is that Asheville has the "best educated wait staff in the country." It's not really a joke. Underemployment is a huge problem.
And real estate here including rent is not cheap when you compare it to the median income. It looks cheap compared to Silicon Valley, but SV also has a lot of high salaries that you'd find it hard to earn here (unless you can telework / freelance / startup). The RE market is distorted because Asheville is a major vacation and retirement destination.
You have to advance your own dreams or career goals. Unlike big, driven cities, the city's culture will not push you. It is easy to get comfortable and give up. (This is a problem outside any of the major cities, honestly.)