Interesting & great topic to stumble upon.
Myself, my wife and family pet are getting ready to embark on such an adventure/undertaking ourselves. At the end of April, we are leaving Yorktown on the TA, and heading westward eventually hooking up with the "western express." I will be cycling and the wife and man's best friend, will drive along in a family vehicle. Obviously our plan is to camp out as much as we can along the way, with motel stays thrown in here & there.
As a successful finisher of the "Tour Divide," simply plopping down just about anywhere for the night leaves me thinking that doing the same on our upcoming travels, won't be any different. I have seen my fair share of other long distance cyclists taking up a resting spots as well as many of you possibly have too in the past, in various locations all along cycling routes. There are lot's of places to hold up without drawing any sorts of interest all across this land of ours - using past experience and common sense no less.
The boredom issue for my wife, is a situation of which I don't see happening in our case. She is wide open to this endeavor and is looking forward to seeing and discovering many things along the way herself. Living in the constant grind of the moving world, it doesn't take long I have found to warm-up quite nicely to those sleepy little towns, or endlessly long roads complimented with picturesque views. This is the only way that she can get out and see/do such a thing, since cycling it is totally out of the question. All and all as I have said to her numerous times, when all is said and done, this experience/trip will end up being one of the greatest things we ever did together. The experience is what you make of it!