Vinnie,
I'm going to try to coordinate this with a monthly trip I take down to a facility in Kentucky that I do for my employer, so I'd be trailering my bike down, not riding. I'd be in the Bowling Green area and leave for Deals Gap (or wherever we're going) either Friday or Saturday depending on what works out best.
You're right, you don't want to get near Chicago anywhere around mid afternoon on Friday. The route you have planned sounds like good idea. I hope you can find somebody who can make the ride with you.
I have enough flexibility with my schedule that I should be able to do this. So put me down as a pretty good maybe.
