Thank you everyone for the comments. They're very helpful. Even considering the limitations of a smaller town (especially food, music and racial diversity) the idea is still somewhat appealing to me. I'm getting tired of the big city for many reasons, and think it might be fun to "Thoreau" (you know, how he went into the woods to live "deliberately" for a while) in a smaller town. I figure if I hate it, I can move back and will have a new appreciation for everything that annoys me now.
Justamom, in theory, I love the idea of moving within driving range of Chicago. However, the problem is that I want to GET OUT of the midwest. I want to live somewhere with a different climate and scenery -- probably a town along the Oregon coast (and near a cool city like Portland for weekends when I need some city fun). It's too cold and hot for me here, and every winter and every summer I am miserable. Also, I'm not very attracted to the idea of living in a smallish town in the midwest -- I don't think that would suit me and I'd be better off somewhere "west coast."
Also, justamom, I wish I were a vet!!! I'm an attorney, but if I move I won't practice law, first of all because I'm not licensed in any other state. This is good with me, because I don't want to practice law any more!!!
I'm wondering -- when smallish towns are discussed, they're usually described as conservative, everyone knows everything about you, etc. Is this the same if the town is more like a tourist destination? The communities I've been considering are pretty touristy, and I'm attracted to the whole transient atmosphere and the idea of having new people around all the time. I wonder if smaller towns that attract a lot of tourism have a different vibe than smaller towns that don't. Is this true?
Also, my boyfriend would be coming with me, so I wouldn't be alone.