Don't know about the rotation personally...but they turn out good docs and it's a beautiful place to live. Where to eat, I've got that one covered...I went to undergrad at UK and my parents still live in KY.
Upscale
Steaks-Malone's
Italian- Sal's, Portofino, Bellini's
Merrick Inn
Murrary's
Dudley's (one of my favs)
Cheap eats
Gotta go to Ramsey's (good southern food)
Tolly-Ho for a greasy burger and great milkshake (opened 24 hours a day)
All of the Indian places are good, thai okay (Bangkok house if probably the best...and it's not great).
Pizza- Joe B's
When are you going to be there? If it's in Oct. you have to go to Keeneland.