I led a club overnight ride for noobs a few years ago to Santa Rosa (Tom, weren't you on it?). Everyone had a blast. And quite a few learned some valuable lessons on setup, gear, luggage, etc. One guy had a yard sale of gear, sorry can't remember who it was, for about a mile down a trail because he tied everything down with bungee cords. Bungee cords don't work for what we do. We fixed him up and got back on the road and everyone had a laugh over it. God, who was it??? Anyway, these types of rides are an excellent resource for noobs to learn. I've ridden thousand and thousand of miles off road in remote areas camping off my bike and am constantly learning and changing things up. I think I have three full sets of bags, tents, gear, etc, that I went through before I got a pretty good grasp on the way I wanted to do it.
Here's a pic from the top of Santa Rosa