A couple of quick ones:
* Don't use bungee cords to secure stuff on your rear rack. Instead, use a bungee web. It's many times more versatile. You can always secure "one more thing" under it. Bungee webs are available from REI and other stores/websites. About eight bucks.
* When touring in out of the way places (which is just about everywhere on the TransAm), don't assume that the local bike shop has the item you need in stock, including common items. Call first. One shop I visited didn't have Halt! dog spray; another didn't have my tire tube! I wasted about twelve cycling miles to get to those places.