I moved back home to the small/medium city in northern wi where I grew up. 65k people, with about 100k in the metro area. I love it for where I'm at in life right now, great schools, cost of living is reasonable, pretty good bar/music scene with a small liberal arts college here.
I never wanted to move home, but some things I'm liking better than expected, some things are worse. Having a big city about an hour away for better stores and real cultural options is huge. Having a decent employment base and housing is huge. If you're single it can be a lot tougher to meet people, my wife and kids and I are basically a unit but we don't have much in the way of friends. Dave chappelle is doing the same thing, living in a small college town in Ohio, he gets it, they are out here, but you gotta be more self sufficient, easy to get depressed and lonely, it's easier to blend in, in a bigger city and you will find cool people by accident ... You gotta know yourself if you can handle making friends and discovering fun stuff on your own without it being handed to ya.