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I used to live close to Nashville and had some business interests there too, so I'll share my recollections. As you saw, it's a beautiful setting, with tons of shops and fairly easy access to both Bloomington and Indy. It's basically a tourist town (some would call it a tourist trap) and also has a lot of retired folks living in and around town.
In the fall, it's a zoo, with thousands of people descending on it to pick up goodies and to watch the leaves turn. Brown County State Park is nearby, as is Monroe Reservoir; so there's plenty of outdoor activity within an easy drive, when the highways aren't choked with tourists of course. The rest of the year, the traffic isn't so bad, except on weekends. The IGA is a decent food store, although it's more expensive than the selections in Bloomington. Current gas prices probably cancel that out, however.
Real estate prices are comparable to resort areas in the Rockies, Florida, and other "destination" areas. It's considerably cheaper to live in rural Monroe County, the next county west from Brown County and the home of Bloomington. Brown County has always been an expensive place to buy a home, and there's no end in sight. If I was looking to buy there, I'd be sure to get a good building inspector from out of the immediate area to look things over. I know, from a close friend who lives there, that there are "issues" with the local building department and the building industry. There's some pretty shoddy stuff being put up, along with some incredibly well done places as well. Caveat Emptor.
There's a lot of small town politics, as one might expect; and there have been some scandals off and on over the years. The schools are pretty good, but they're hampered by low funding levels and overworked teachers.
If you're not from Indiana, a few words about the weather. It's hot and muggy in the summer, with 90+ degrees F with 99% humidity very common. Spring and fall are likely to be rainy; and winters are damp, cold, and grey. The bad weather tends to set in at the end of October and really doesn't let up until after Memorial Day. There might be a couple of feet of snow, spread out over the winter, but it tends to melt off between storms. Icy roads can be an issue. Winter can be pretty bleak, spring beautiful with flowering dogwood and redbud, summer hot, and fall nearly as pretty as New England.
The area still retains a great deal of agricultural charm. Getting stuck behind a tractor or a combine on Hwy. 46 or 135 isn't at all unusual. Watch out for deer, particularly at night! If you don't mind the hordes during that 6-8 week stretch in the fall and can afford it, it's a nice area.
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