What I wish from Trump is for him to be totally honest. Why are you running for the highest position in government when you have zero political experience, I'd ask him. I mean, come on, even President Reagan was governor of California for a while before being elected!
And something like this is what Trump could say,
It's true I haven't any political experience. I am a businessman like my father. I grew up with money and it did make some things easier. What I am interested in is what I have to pay in federal taxes. I have been audited every year for quite some time. I would like to change a lot of things so wealthy people like me can keep more of our money.
Voters can evaluate that then decide if they agree or disagree and it can be that simple. If you agree, you have the right to vote for him. If you don't, vote for someone else. There's no shame in disagreeing with him, or agreeing. It depends on many factors in your life not just on how much money you have. So why not be honest about it? Can't alienate any more than already.
What I would like to ask voters is, what if you needed some sort of life saving medical treatment and this doctor appears. You ask, say Doc, what kind of medical experience do you have and he tells you none. He started yesterday and they hired him off the street. Before that he was running a real estate office but now you trust him with this life saving procedure, that he will know how to save your life. He will magically know what to do, so you can trust him, right?
Same goes with lawyers. You've been charged with a felony crime with your liberty at stake when you know they nabbed the wrong person. They send you a lawyer who never went to law school, never stepped foot in a courtroom. He's been successful running a business with a few scrapes here and there but he never studied law. Suddenly he's a lawyer and it is he who will help decide your fate for years to come. Would you put your trust in such a person only because he knows exactly what you want to hear, or would you rather have someone who graduated law school, has passed the bar, and has a few years experience trying cases and at least won a couple?
POTUS is just as important, if not more, than either of these professions yet so many are willing to elect a fast talking businessman who has never proven in any way he can handle being a politician. It is kinda scary.