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Well, I can think of few reasons people might like Trump:
1. Speaking his mind:
Plenty of republicans who share his views but live in a cultural mindset that they are not alright to say. I know this because when people used to mistake my libertarian preferences to mean republican, they'd often assume I was part of the club and just spew that shit with me - "I don't believe we should let black people run the country", "I don't believe a women can govern", etc. But most of the time in social situations they try to maneuver around saying it. Can you imagine how cathartic it could feel for them to hear someone saying things like this out loud?
2. Jealousy for his lifestyle:
Plenty of people fantasize about been all powerful billionaires, plenty of people look at his luxury lifestyle with lust, plenty of guys would like his wife for a trophy. Really, who wouldn't want to give children a helicopter ride they'll remember for a lifetime? Where there is jealousy, there is often also admiration, and that can create glasses through which he'd seem a lot more charming then otherwise.
3. Frustration with the current system:
Bruce is right on that one. But it's more then the middle finger, to some extent it can be justified. Every other politician in the race is going to be backed up by lobbyists and interest groups from everywhere. It's kind of ironic, because voting to trump is kind of like jumping over the politician and voting straight to the financial backer, but the result is that he appears uncorruptible. Realistically, he still runs multi billion dollar companies and will be in a position to give political favors with financial returns - something we saw quite a bit in the Bush administration, but this could take it to a whole new level.
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