haha I'm not sure if that makes me feel any better...
I'm in a super agnostic place about Trump right now. All the political scientists are saying that there's no possible way Trump will win and his support will inevitably collapse.
But a) they mostly all said it should have ALREADY collapsed and moved back the date, and b) they also all think that nothing particularly different is happening this election cycle, and I don't agree with that. I think there's a realignment happening and party power is very weak until the coalition becomes stronger.
So the answer to the question really depends on how you feel about party power. If the party still has significant power to control what happens in the primaries, then Trump can't possibly win, because the party hates him. But if you think that superPACs, coalition fractures, loss of earmarks, hatred of the establishment, etc. has led to the party losing most of its power to control the primaries, then not only COULD Trump win, it's very likely he will.
The split the difference position, which I'm tending to suspect right now, says that Trump probably can't win, but that some slightly more respectable but still outsider candidate can win with his support. In other words, Ted Cruz. Cruz is buddy-buddy with Trump for a reason, he has the "insane person" bonafides to win the dark end of the Republican base, but he's also, no matter how much the GOP Senate caucus might hate it, a GOP Senator, with campaign experience and government knowledge. The party hates Cruz too, but it just can't hate Cruz as much as it hates Trump, because you can't really throw a sitting Senator out in the cold like that. If you forced me to predict the election, I'd say that Cruz hangs out, sucks up Carson and Trump's support, and ends up with a narrow victory over a more establishment candidate (although they're all sucking so bad right now I don't know which one, probably Jeb!).