I don't mind the ride out west - I want to do the ride and experience it. Maybe in some years down the road I'll do trips where I ship my bike somewhere, but I'm not there yet.
Thanks for the reminder about the high winds and I've read of many riders saying some of the winds across the Midwest can be really intense and draining. I cross my fingers and hope I get lucky.
I've already been thinking about what to do about timing Chicago. Right now I think I will leave home around 6am on Saturday morning and find a place to crash west of Chicago, so even if I get slowed down by it, then I don't have much further to go that day. If I don't get slowed down by it, I can get an easy first day in and be well rested for the next day, or I can try to go as far west of Chicago as I can in that first day. I know that the second day will be a longer day to get me as close to The Black Hills.