Hey Brock,
Looks like you AZ boys have a pretty good group of TW riders and some neat places to ride. Keep the ride reports coming!
You are right about maybe needing some extra support for the Pelican case and storage tubes for off-road riding. A few weeks ago, my son and I were riding on some national forest land adjacent to Yosemite. My son was riding my TW with the case loaded up pretty good and two full fuel cells in the storage tubes. I was riding behind him and could see some wobbling as the fender was flexing, but it wasn't too bad.
I didn't see exactly what happened, but as I came around a curve I saw that my son had dumped the TW pretty hard on the left side. He was okay but the impact on the left storage was enough to dent the aluminum fuel bottle inside. It also pulled out two of the three threaded inserts holding the case to the rear fender. We were able secure everything with some zip ties and nylon strapping and complete the morning's ride.
There was no real damage to the bike as the storage tube and case took most of the hit. I have since remounted the case using longer bolts and fender washers on both the case side and the fender side. The good news is the case is less likely to come off again, but the bad news is if it does it will cause a lot more damage to the bike.
Brian