There's something to the Joy Reid remark in the above twit.
A big part of this does go back to the 1980s and the ways that Trump used to attain fame. He knew that being given a lot of stuff wasn't enough for what he really sought. His gameplan was to, as Charley Steiner and others describe in the 30x30 episode about the USFL, get himself on the sports page, and then the gossip page, and then onto the front page. He wanted an NFL team but settled for a USFL team and then was the leader on the mistakes that doomed that alternative league. He pushed for a rapid expansion of teams (for money) and a fall schedule (for attention). Two Wrestlemanias and a lot of big boxing matches followed at the Atlantic City casinos he bamboozled his way into owning. More attention. And, of course, he's such a dipshit he bankrupted those casinos in a town where people fly in to literally give you their money.
He deliberately had public and affairs and messy divorces to get on the gossip pages and, more importantly, the cover of supermarket checkout aisle tabloids. The folks who voted for him (no, they do not need nor do they deserve defense or pretzel-like contortions to rationalize) believe in those magazines and they're ones most likely to see them by doing their own shopping.
It wasn't a thing in the 80s so it wasn't part of that effort but, once it became part of America, he jumped right into reality tv. Other than the tabloids, and maybe sports, there's nothing more effective with this large, sweeping demographic than reality television.
He homed in on the dumbest aspects of the biggest demographic and it has served him well. I find it an embarrassing reality about Americans.