Northern part of Illinois: don't really want to go back. Would go to Chicago if I had unlimited funds. I love the different cultures and cultural stuff there. Shopping is great, all pro-sports are available. And with unlimited funds, I could leave in the winter, if I wanted to.
Charlottesville, VA: Would not go back. Too expensive and way toooo snooty.
Durham, NC: not bad. Close to beach. Very hot in the summer, winters are fairly mild, most of the time.
Omaha, NE: would go back in a heart beat. Nice people, affordable. Weather can be wicked.
Key West, FL: lots of fun, have to deal with tourists. If a hurricane is forecasted....there's only one road to safety, and everyone is on it.....or an incredibly expensive plane ticket. You don't get a good price on a ticket, even in the case of an evacuation.

(mine was $900)
Springfield, IL:

Roanoke, VA:

Outside Scottsdale, AZ: snakes, scorpions, endless amounts of sand.
Asheville, NC: pretty, small, lots of culteral events for such a small town, liberal, closer to the Carolina beaches.
Eastern TN: pretty, summer has apparently started since it's to be in the 70's for the next several days, fall doesn't start until mid-late October, winter is short, people are nice, not a lot of different cultural stuff, UT football is a way of life in the fall, UT basketball takes up the winter, 5-6 hours to Carolina beaches, 8-9 to northern FL beaches, no state income tax for individuals, housing is reasonable.