Last year, I read one of Trump's Entrepreneurial books which drew heavily on anecdotal evidence from his own life. This is what I gathered.
His saving grace seems to be his sense of life, which is very thoroughly the American kind of outlook that Ayn Rand praised so highly. He aims high (in every concrete or practical endeavor) and refuses to accept failure as permanent or inevitable. I think this is a large part of his appeal.
That being said, he has absolutely no explicit grasp of what makes those traits valuable, why one should strive to have them nor even that they can be gained or lost. He chalks his own bravado up to some sort of innate idea, which he just can't help.
What's worse, he makes no distinction whatsoever between the public and private sectors. In one part on brainstorming business ideas he included nonprofit, charitable and political organizations together as different kinds of "businesses".
That's the real danger I see - that he's going to wield his guns as if they were dollars, and we will all be on the hook for it.
And I think he's going to win.