Ahhhhhh yes I know ;) and lovley small towns they are too. That area is my second home. Hopefully one of these days I will be blessed to make it my permanant home. E-town is the closest for shopping etc, and has GREAT flea markets. I like Leithfild also.
Mom says a lot of folks move down there to get away from the blue states, but then a lot of them try to change it into what they were escaping. Don’t let that happen!! One by one, my family will be/has been relocating there, and NOT to change it!
They also enjoy being closer to their families in Chicago, Detroit, Cleveland, New York, New England, etc... A lot of these families couldn't necessarily afford to travel all the way to Florida and stay a week in one of the tourist-trap hotels down there, but they can usually handle the prices here in Kentucky.
Louisville is home to a large number of excellent hospitals, including one of the finest heart hospitals in the country, so they don't have to worry about health care.
Additionally, there are all sorts of activities to keep them entertained. There are a number of wonderful golf courses in Louisville and Lexington, the tracks at Churchill Downs and Keenland are always packed, and there are a number of fine casino boats lining the Ohio River (I don't gamble, but they do have some of the best restaurants in the area for pretty reasonable prices).
If their interests are more in the line of shopping, Louisville, Lexington, Cincinnati, and Nashville are excellent choices (my mom and sisters are shopping connoisseurs) and there are also one or two antique stores in almost every little town in the state.
A surprising number of these folks are more red than blue.
By the way, if you like flea markets, Louisville has a huge one the last weekend of the month at the Fair and Expo Center. The room is somewhere around 100,000-120,000 square feet and is stuffed with just about everything you can imagine, and then some.