I have to say that this election cycle is Trump's to lose at this point. The only way he doesn't win is if he drops out or self-destructs in some other way.
I don't think the media can touch him. He's been a controversial public figure for so long that there's no way the media can redefine him.
With the large following on social media Trump already has (and it's certain to explode), he can easily bypass the conventional media to get his message out.
He's got millions of dollars of his own money to burn and he won't even need a lot of it. Just a cellphone with a Twitter account and he'll make headlines whenever he wants. Trump is not afraid to use social media. All the other candidates are running a traditional 20th Century campaign.
Goldwater in '63 and Reagan in '79.
That air of inevitability surrounded both.