What you say seems quite sensible, and yet I wonder. After all Silvio Berlusconi, another obnoxious billionaire clown who could be Trump's twin, won in Italy.I am willing to put up a wager that if it is Hillary vs Trump, she can start victory dance as soon as he gets nomination. The only way to defeat her is some kind of smoking gun (email and Bengazi do not matter).
Trump is popular with his base. Candidate needs more than base to win general election.
May I suggest that if only Silvio Berlusconi were a "Natural Born" citizen of he U.S., that he and Mr. Trump would make running mates ideally suited for one another.