I have met a number of business people who have been exceedingly successful in business, and there has not been a single one of them who has not had business failures, lawsuits, and bankruptcies.
And every one of them has been successful for, among other reasons, daring to take risks, often high risks.
Your post has several different objections, and for the last paragraph, I have no question that he has angered many conservatives; he has also gone down paths parts of the Republican Party would not go. He appealed to the “lost and forgotten” of the unions who have been ignored now for at least a decade and a half, if not more, and union voters were a significant part of his election; they openly mocked Hillary afterwards for her almost total lack of interest in anything they had to say - and specifically, the move by both Democrats and Republicans to move as fast as they could to either move businesses overseas, or to enable other business leaders to do so.
And in both elections, particularly in this last election, Trump obtained greater support among both the Black and the Latino communities; and I have yet to see anything in the past where a Republican President went so far as Trump did in making progress supporting minority businesses.
And neither of those moves were taken from the Obama playbook.
Part of why he has been hated so much by some Republicans is that he has been a populist, a term that was applied to President Clinton when he found himself saddled with a legislature not to his liking - or his party. And this comment is not directed to you - but the Republican Part has for ages been considered “lily white” - a move that at lest in terms ovf voting seems to being put into our past.
Sadly, we have a two party system and the results appear, from a long distance view, to be most effective when the Administration is in one party, and the Legislature in the other. Given the internal struggles within the Democratic Party of the centrists vs. the socialists left win, I am not entirely sure that will continue, especially in light of the US elections (as in, votes for the Legislature, state governors, and state legislatures the target of the Blue Wave that resoundingly flopped).
Me - I am hoping and praying that Nikki Haley runs for President this next time.