I'm not going to defend any of this stuff Trump does. I'm both clueless and trying my best not to judge.
I will say that Trump is sneakily slow playing the electoral college for 2020. How many issues has he "coincidentally" sided with the views of people that reside in swing states, especially the ones he won in 2016? It's a smart strategy politically. There are many states that are set in stone every year as Democrat or Republican. No point in worrying about New York or Massachusetts wants and needs strictly from a political standpoint. He'll never win that state.
He is basically pandering to those swing states now, taking the constituents' sides in those states and giving them what they want. It's quite likely why he has a boner for coal country. You constantly hear him talking about Pennsylvania, Wisconsin, Ohio, Michigan, etc. It's no coincidence. Regardless of who hates him, how much he pisses off Democrats, etc., as long as he keeps giving the people in those swing states what they want, he'll be hard to beat in 2020 assuming he isn't dead or arrested.