I agree about the economic inequality and the emasculation of men by technological progress. I agree also with the libertarian idea of freedom of speech. I come from an arts background, so I have a loathing for censorship.
And I take your point about the Senate as a break on democratic mob rule. In effect, though, the gridlock from the structure of the American government blocks democratic initiatives that would favor the majority, while the rich minority get their interests passed through their special access to the politicians (via their huge campaign contributions, full-time lobbyists, the revolving door to the private sector, and so on).
Also, I think you understate the element of racism in Trump's electorate. Most Trump voters aren't as down and out as you'd expect. What many were reacting against was Obama's blackness. That's what "Make America Great Again" means to a lot of these voters: "Make America White Again." And "Stop the Steal" is another dog whistle that refers also to the steal of white power by immigrant minorities.
You certainly understate matters when you say Trump didn't "understand" how republican government works. Trump literally said out loud and in public that he and Kim Jong Un "fell in love." As a Russian asset (a useful idiot of the KGB, groomed since the 1980s, as the link below suggests), Trump is an authoritarian who prefers dictatorships to free societies (as long as he'd have the power to rule).