Wow! This looked like it was a lot of fun! I just checked and according to Google maps its a 1700 mile drive for me, holy crap. That's a long way to drive if especially if something got damaged on the Jeep.
You bring tools and some spare stuff and deal with whatever you have to. Ride slightly easier trails. I generally do the hardest ride of the event the first day so that I have a couple days if something goes wrong and then go easier the next day(s). This year I didn't get to do that because I was voluntold to lead a scenic ride the first day, but it was fine.
This trip I had spare driveshafts, front axle shafts, a stub shaft, u-joints, fuel pump, oil filter, tie rod, tcase/axle yokes, hoses, and more that I can't think of with lots of little nuts/bolts/wire/fuses/connectors/etc that I generally always carry.
Thanks to my electric radiator fan going out, I now have a spare fan setup (bought at NAPA in Moab and just put in a new Contour dual fan yesterday) that will be going along for future trips.
Driving out and back turns the trip there/home into part of the fun. With as many trailer and truck problems as seem to occur every National, I don't feel like my odds of having an issue are that much different than folks that trailer.