I would stay in Frankfort--only about 45 minutes to Churchill. Or stay in Indiana--probably Scottsburg which is about 32 minutes from the track. Rooms are so much cheaper in those two places.

I would go to the Oaks and Derby.

Eating - Ginny's (hamburger joint), Lynn's Paradis Cafe (breakfast), Proof (hip and fun for dinner), Ramsi's (food from all over the world).

as a twin spires club member I get them every year. I kept on applying until i got them. I applied year after year. Started getting them 5 years ago. Once you get them you get priority for the following years. Tickets don't come "in hand" until April 1st, but you have to pay for them by Oct 31

I really appreciate all the feedback... It is going to be very helpful...