The fact is that most Americans, and probably all Americans who might even consider voting for Trump, absolutely hate taxes. If they could get away with paying as little as Trump, they would. In fact, I'd hazard a guess that, even if most Americans don't explicitly cheat on their taxes, they probably play a little fast-and-loose on claiming deductions, and are not quite sure about whether they might not have made an error in their favor. They probably worry about the eeeeeeeeeeeeevil IRS auditing them, and finding something they thought was innocuous over which those eeeeeeeeeeeeevil bureaucrats would delight in sending them to prison.
Even the word "tax," repeated over and over, creates negative feelings for most voters. My guess is that the response of many to that ad would be that "Yeah, lots of ordinary people pay way too much in taxes...and that's because of those liberal tax-and-spend Democrats. We need to vote Republican to reduce our own burden."
Instead of playing "but his taxes!!!" -- it might be wiser to frame it as revealing that 45 is a pathetic fraud who has been presenting himself as some great success when, in fact, he's a complete failure.
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