Let's see..
1) The postman and the janitor go to Wharton too. Every day for years. So what for Donny?
2) He's a mafia "billionaire", not a real billionaire. As soon as the Saudis and Pootie withdraw their favour, and he pays his taxes like he should have, Trump is going to be so far in the hole to debt that he will never see daylight again.
3) No, he's traveled to his own five-star hotels in a few places in the world. They are all the same, so it's like home wherever he goes - gold gee-gaws and hot and cold running slaves to do his bidding. Trump has never mixed with anyone outside of his hotels or golf courses. Put him in the middle of a London street unaccompanied and he will not know what time it is let alone which city or country he is in.
4) His critics are apparently "the elites". Or so we are told. You know. The ones who are supposedly stinking rich and sound like Charles Emerson Winchester III? Hardly the poorest, least educated, least traveled people in the world. Or are you referring to the growing mixed US populace who view Donny as an eminent threat to the existence of their nation? THOSE "uneducated masses"?
5) Of course Trump is alien to them! Of course they view him with hostile comprehension. He is alien to most of the rest of the globe, and the human race. What's not to comprehend? Trump is a charmless, soulless, brainless criminal blitherer and grifter. How hard can it be for YOU to see this, Dinesh, if the uneducated masses already can?