I haven't been involved lately, so my frame of reference is old. It became clear to me I was way beyond my means after the 2008 Rubithon run. Kirsten didn't have a good time at all, I spent a lot of money prepping the truck and spent more fixing it. Just not my cup of tea. I should also admit that my tolerance for 'hard' has been slipping. I just don't really much care to chase some never achievable goal, we've been having more fun poking around back roads in an almost completely back-to-stock truck just like we did 15 years ago when we first bought Imelda with her 225/75R15 Bridgestone Duelers and bench seat. This is I think the fundamental similarity, it's about seeing new places, spending time together and not tackling problems. The runs you list are fine but we've done them a dozen times. Ho-hum. And God forbid, we shut off the engine and hike and ride the bikes a whole lot more now.
'91 Toyota Pickup
'09 Kawasaki KLR650
'12 Gunnar Rockhound 29
"They say the test of literary power is whether a man can write an inscription. I say, 'Can he name a kitten?'" -- Samuel Butler