Does holding office actually matter? Being president is a management job. Resource allocation, brokering deals, and managing interests (taxpayer vs. party vs. lobbyist). Things that the CEO of a billion dollar conglomerate is probably experienced in.
I highly doubt Obama drafts or even reads any of his bills. He probably writes (or receives) a list of provisions, has the bill drafted by some idealistic kids, receives a 5-6 page summary, and signs off on it.
I also doubt Obama's knowledge of the middle eastern and world history is better than a postdocs. He has advisers who give him options, lobbyists who tell what to do, and a party at his back. I imagine a large amount of his job is pressing buttons.
I don't support trump, or anyone for actually. But I doubt he'd be worse than any prior presidents. I also question how much "experience" holding office actually matters. At the end of the day the president can be a genius with decades of experience, but if he doesn't act in the interests of taxpayers none of his experience or intellect matters. Put another way, just because a person knows the right thing to do, doesn't mean that's what they'll do.
This kind of scratches at the problems I have with politics (and democracy) as a whole. Personally, I don't really think the president matters. I'd prefer to have someone entertaining. And Trump is a good showman.