I like to plan, but the planning isn't so micromanaged. I would like to go out this way, but if it doesn't work then this way, sort of thing, have the alternatives weighed out in advance. And plan for the 4th day on the road a rest day.
The Telluride Festival is a high light (two MN bluegrass bands will be there: Trampled by Turtles, Pert Near Sandstone). Rushmore, Devil's Tower, Custer Battlefield, Glacier, Yellowstone, the Tetons, Salt Lake City, and Dinosaur National Monument are also highlights. I hope to do it all, at least that's the plan. It is what to do with everything else. The apartment will be okay, worked out with the landlord, its just the junk of living that we collect. I need to get it out of the apartment, just like I need to get out of town for a while.
One of the jobs is for a bike tour company, it would be cool to get paid to bike tour(not going to get rich). I wouldn't be going to Telluride, but might get the chance to pedal the Northern Tier, and get paid.