You should visit SEVERAL areas before you make your choice
I'm from a small town near Madison named Waterloo. It's about the size town you're looking for.
I thought it was great growing up, had lots of friends, etc. However, now when I go back, I realize that the people who seemed the most fun to me as a kid are alcoholics.
It has nice people, nice churches, a great school system, but as with most small towns in Wisconsin, it's hard to get in with the "townies", unless you're a drinker, too...or you join a church. This definitely helps. I've read many different posts on this site, and they're right. Most people haven't left. It's several generations in one town. You have to make your BEST EFFORT to be welcomed.
If you're really looking for a small town in WI, I would suggest visiting the areas a few times. Waterloo is a great place to live, if you want to be close to all things artful, fun, etc. Madison is only 20 minutes away, and they have everything from Macy's to Whole Foods, Badger sports to off-Broadway plays.
I've lived in Chicago for several years, but if I was to move back to WI, it would definitely be to Madison. It's the only place that has enough of what I'm used to to survive.
This area is not "cheap". But, you get what you pay for.
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