Doesn’t matter if he doesn’t understand conservatives, they’re going to ( on the whole) vote for Trump. It’s a question of what the mushy moderates will do.
I lived in MA when Scott Brown ran for the Senate and won, and when he ran and lost. He was not an impressive candidate. He won the first time because not even liberal MA wanted Obamacare shoved down their throats. He lost to the fake Indian because there was no longer any rationale to elect him.