Hey, I'm originally from Middletown, Ohio! Haven't been home in a long time but it was nice to see a familiar town on the board.
As far as your trip plan it sounds really good but the only word of caution I would give (Being a die-hard commando type) is to be flexible and if for some reason the family is too tired to really enjoy the day, stop and take a break even if it's not on the schedule. I practically ruined our last trip in 2001 because I felt the need to STICK TO THE PLAN! We were sitting in 50's Prime Time Cafe and I was so tired that I was miserable and didn't get to enjoy it at all. I would have been better off calling it a day earlier and trying to head back there another day.
Have a great trip.