About our luggage:
Erik had mounting problems with his Ortlieb side bags throughout the trip. The lack of proper side racks for the X Challenge, and having to use zip ties and short Velcro straps to mount the luggage took their toll on the bags just after a few miles, which is why we see him making adjustments early in the first section. Luckily, our partner Mike had some of his trusty green webbing (can be seen holding the bags across the bike) with buckles which saved the day once again. (Mike had to use the webbing to strap a broken rear rack together before).
Mike had proper racks on his KLR which he made himself. He was running Ortlieb bags just like Erik and had extended the Velcro straps that cross over the seat area of the bike, so they held much better. One issue he did have with his side bags is that one side developed a small V like cut in the "dry" material. We're not quite sure how that happened.
I have been using the Wolfman dry side bags with Wolfman side racks and medium duffel on the rear rack for more then two seasons and multiple dirt wrecks and they have done fabulous. They mount solid and have a tone of adjust-ability, however they do have more straps to deal with, and are somewhat dificult to mount and unmount from the side racks. Once mounted, you don't need to unmount during the trip unless it strikes you're fancy.
One thing about the WABDR is that it will rattle your teeth out. I learned that you really need to have your gear strapped down, and your nuts and bolts tightened up. I lost my spedo, and tail light to the vibration and bumps going down the trail.