I think it's because he has very complicated tax returns, that among tax accountants and lawyers are perfectly legitimate write-offs and expenses, but that Democrats would oversimplify and exploit in campaign ads to demagogue Trump as an evil rich guy.
That's a legitimate answer (I won't deal with the rest, as you've gone off piste). But GW Bush and so on, who I understand has a lot more money than Trump, did it. And Bush was as reviled by parts of the media.
If you're in the public eye, that scrutiny is just one of the prices to pay, isn't it?
