I have done loop tours in MT and SD. Ship bike (with racks, stove and fuel bottle in the box) to a LBS. Fly to the start/ending location with a bag with the rest my gear. Shop assembles the bike and has it waiting for me. Shop holds my bike bog and gear bag. At the end of the tour, give he bike, stove and fuel bottle back to the shop along with sipping document, get my bag and go have a beer.
When I did an up and back on the GAP, I drove to Cumberland, MD and left my car in the free lot under I-40.