DBM: Double quote.
I think you may be right. A number of my wild brain-wrestling includes him heading back to one of the places they landed over the course of both of road trips where they may have met some interesting characters. We did the cross country thing for just one month, and I met and spent time with at least 6 curious people/groups of people that, after spending time with them, would have been excited about hiding me, if I showed back up and had a great story. Stick it to the man, and such.
The reward does makes that harder to trust, THOUGH, a handful had not much use for money, had loads of it before, hated the lifestyle and walked away to a sort of nomad life. (Or so they liked to talk about, anyhow) The whole "off the grid" crew is diverse.
Maybe he is just really good at playing "hide and seek". If he can get away from the cities, rural folks tend to mind their own business, unless they personally feel threatened. Hide in some barns, sheds, abandoned/falling down houses and barns.
While food and water is a need, there is an abundance of farms out there with wells, and half the time, I am not sure they even know who is showing up to work the fields, etc, from day to day. Some workers are just bussed in and dropped off, 20 or more at a time...
The reward complicates things, some. He, so far, has figured something out, for sure. MOO.