TheDecider -pfsjkd -Trump's issue is his poor view of himself. This is why he has to constantly verbalize how great he is and how good a job he will do. Deep down he knows he isn't very talented and that people don't like him all that much. This is the source of his thin skin and the major reason he would make a terrible president.
I think the crux of the problem is that Trump has a typical New York trait (bear with me, OG NYers before you vote me down into Bolivian) and you couple that with the entitlement he's had his whole life being rich and it's just a recipe for disaster.
I've met quite a few people from NY, many are very cool, like our own Nitecrawler. But among many of them is a weird trait. It's a kind of self-centeredness that runs very deep and is virtually impossible for the people who have it to admit to or see in themselves at all. If it's not important to them, it's not important. Period. Literally. It doesn't matter at all.
I have a friend at work who's from NY and loves everything about Trump. Like Trump, he literally cannot admit that he's wrong and he cannot admit that Trump has done anything wrong because all the shit Trump's done isn't a big deal to him. He thinks the election is rigged because of the people who DO take issue with the many, MANY verbal gaffes Trump has made are making such a big deal about them. I mean it's obvious!! Who cares about any of that stuff?? I don't, so therefore, they're not important. Period.
This trait at its worst comes out as a really bad hypocrisy that the person just CANNOT see. Much like how Trump thought the whole Clinton impeachment was 'over nothing' and the Clinton victims were 'losers' way back when.
If Trump had been able to just *pretend* to be likeable for 5 minutes and had the least bit of substance to his policies he would be looking at a Reagan style landslide over HRC. Now, it's very likely to be the exact opposite because he's completely incapable of even acting like a decent human being or taking smart direction from smart people looking out for his interests.
He def has some insecurities, like his hands. But I think a lot of his douchebag behavior is rooted in his narcisissm and the belief that he actually does deserve to grab any woman he wants, doesn't ever have to apologize for being 100% wrong, etc. It's naked arrogance.