Depends on the person. Some have a deep-rooted distrust based on hearing and seeing quite a bit of information (and we all know that the information we use to process reality is half-true at best); others don't have any prejudice (not saying prejudice is a bad thing) and will naturally be easier to bring on board.
I agree with you, his appeal is unlike that of a politician. Even some Bernie supporters have Trump (not Hillary) as their second choice.
There is a gamble of sorts with Trump. But after gambling with people of our own party over and over and over,McConnel, Boehner many others and watching them do the wrong thing as recently as Paul Ryan giving in to both Boehner and ozero. Some don’t see it as much of a gamble.
Let’s face it, Ryan screwed us on the budget and the debt ceiling all in one fail swoop. And for what reason—none given.