Giggles! I'd have to answer this post in multiple sessions as you covered a lot here while I feel like those travelers in the 2nd picture most of the time. More about that later perhaps.
Having grown up as a nomad, mas o menos, I have no illusions about any place being fundamentally better than another. I usually travel for specific reasons that include, but aren't limited to: I don't want to be where I am right now. My interest in the Hills has mainly to do with air quality, I like to breathe, climate and population. Of course this is offset by the fact that hilly terrain is harder on old bones, so I want to find a place that is flat enough to walk on, and high enough to ensure that polluted air doesn't use my lungs as a filtering medium on a constant basis. L.A. and Bogotá in the 70's were good examples of that.
Most of your observations ring true with me and I never saw society as something other than a wealth collection device that doesn't care much for it's components so long as there are enough of them to function. I never felt the need to join any particular group, club or society, probably because moving 17 times in 10 years made me realize at an early age that the dynamics of any group would eventually make it behave like most others. That doesn't mean I like to live in isolation either.
RE: Conversations in my head.