You know, I was just thinking how reality may just come to bite him in the tush in more ways then just the elements on this trip. First off, he may find out that just like mom and dad, other people may(read will) expect you to work for something. Even the 'sweet liberals' who seem to want nothing, will probably be rifling through his bag for something of value when he's catching a nap.
Now, when he does find the hospitable person out there, of which there are many, it may shatters his small liberal existence to find that conservatives are nice people too.
I actually think since nothing in this person's 50 something year existence has opened their eyes, that perhaps interacting with someone other then DUers outside of his family members may be just the thing to nudge along at the very least a little tolerance(don't they love that anyway?) of the other side. After all, those he will have to depend on the kindness of aren't likely to all be liberals, especially if he's venturing outside of the larger metropolis areas.