Dustin, thank you for your thoughtful and in depth analysis. I'd like to add one important element or angle to the psychology of the moment. The ways in which modern technology have hijacked attention also make it more difficult for people to connect with what is meaningful.
Prior to our immersion in an Attention Deficit World, Trump would not have even been a viable candidate - he doesn't even talk in discrete sentences. We have been programmed to react, rather than to reflect, and Trump does a masterful job of tapping into that - and he also pushes all of us into a more reflexive, less reflective mode of being.
The last third of my 2019 book, Recognizing Adult ADHD: What Donald Trump Can Teach Us About Attention Deficit Hyperactivity Disorder, goes into this aspect of our changing world in more detail.