I've also suspected these manipulations, strategic bankruptcies, and moving debt, but that doesn't make him a successful at doing business, it makes him good at cheating the system. We also know he does make money from selling his name, which will stay afloat as long as he can stay afloat. But, again that isn't business, it's a cult of personality.
Really, before this election I never really thought about or questioned it, but now that he's exposed himself to the world, it has raised far more questions about him than it's answered. And one of those major questions is how does someone who gets defensive over his hand size, mocks the disability of a journalist who reported things Trump didn't believe in, and gets into a Twitter war at 3 - 5 AM with a former beauty queen and telling people to watch her non-existent sex tape make it in business without being eaten alive? Successful and powerful politicians and executives cannot afford to be as careless and brash as Trump is. If he wins, he's starting with very few allies and tons of enemies. It's almost like he has no foresight, because he was able to gain in the short term with a surprising (but not surprising in hind-sight and once facts are known) primary win, but when it comes to what really matters at the state level, he has nothing. He's offended so many Republicans and Democrats that he may just face worst obstructionism than what Hillary will face or what Obama has faced, and he has brought it upon himself.
He's shown he can cause a short-lived feedback frenzy loop of feeding the people who feed his ego, but the debates have shown us he is delusional and looking exhausted.
No, but everything to various degrees is a personality contest, and Trump has not shown he has the personality or characteristics of someone who can be successful at politics or business. If he really gets upset over someone saying he has small hands (which is a seriously WTF? type of insult to begin with), what are his business dealings really like because business, especially high-roller international business, is not for the weak.