I still maintain, the issues you have outlined are powerful but demeanor at this point is everything.
I like your idea, but if I were Trump, I might use the debate format to attack Hillary with a bill of particulars as you suggest. He would have a much larger audience, and she would have to lose that irritating smile or its falsity would become even more apparent. Pretty much any question can be turned against her. Any question on foreign policy could be turned onto the disaster that is Libya, Syria and the Russian reset. A “woman’s issue?” Her disgraceful treatment of Paula, Jennifer, Kathleen, and Monica. Trump’s taxes? I’m pretty sure the Clintons must have some interesting deductions or capital losses on their returns. Tax policy? Increased rates hurt the middle class not rich folks like the Clintons, who can afford fancy lawyers and accountants. National defense? She was the one who put the nation at risk by putting its secrets on an unsecured server and then obstructed justice by having her underlings bleachbit it. Income inequality? She’s the one who made speeches to Goldman Sachs at a quarter million a pop, which speeches she now will not release. It would not be difficult,
I still maintain, the issues you have outlined are powerful but demeanor at this point is everything.