Just for discussion and knowing extra driving would happen, what I worked through in my mind was something like this:
Spring: Leave KY go up through IL to WI, across ND, MT, UT, to WA down through OR, CA and across AZ, NM, TX, LA, MS, up through AL, TN back to KY.
Fall: Up trough IN to MI and across around down and back up. It was just thinking of options. I really lean towards Srping and Fall traveling with something at home or stationary in Jun, Jul, Aug.
But I'm pretty open to anything that works. Just think it would be aneat trip and with someone else to enjoy the time even better.