Sorry to hear about the bum ride. I've only taken solo rides. I carry an InReach and file a flight plan with wife and friends before leaving. No payload left for anything heavier than a strap, so I just roll with lots of confidence in myself. If you want a good laugh, here's the chronicle of my first moto trip, a solo on the AZ Traverse,
http://www.expeditionportal.com/forum/threads/70118
Looking back, I'm actually pretty lucky things went as well as they did, and I had my share of drama. I doubt I will ever be able to manage lifting anything larger than a loaded KLR650 in field conditions. I did the UTBDR this past June/July. Honestly, if that gave you a hard time, I would advise a lighter bike or different routes if you like flying solo. If you are set on your bike, ride with friends or roll the dice
Overall, I think the UTBDR is pretty easy compared to the AZ Traverse.
But what do I know, I've only done 3 rides, one of which ended in a SAR mission