I don't fault Annoying Orange on a personal level for not paying taxes - if the opportunity is available to you, it is not unethical to take it. The tax code is created in such a way that it is possible for very rich people to not pay taxes, and that's the IRS's fault, not the taxpayer's.
But when you promise to 'close the loopholes' after taking advantage of them for decades, it makes you look like a hypocrite and a liar. And plus, even though he'll serve as President if elected, he'll still be beholden to the businesses he owns, and there's no way in hell he will close any loopholes that he can still benefit from as a businessman.
Come on we both know he was bluffing. Theres no way clinton is ever going to release those emails.
I don't know if she even can. I think the FBI would have to approve of it, since some of those emails probably still count as evidence.