"We need to have empathy for those people" because of "those people" is exclusive, but "We need to understand you people and empathize with you" is also exclusive. Is it the "you people"? Or should she have lied and said "I'm one of you". I don't know if it matters because she didn't say that anyway. Then the "I love the poorly educated", which is also a "[them]" is inclusive.
"She clearly doesn't even consider the possibility that a poorly educated person who's leaning Trump would even be in the audience." She made that speech at a fundraiser. Why would she speak to someone who maybe was there isntead of the people that were? What did Trump say at his private fundraisers? Should we compare stump speeches?
Did your hypothetical voter hear Trumps speeches where he constantly mentions how rich he is, how much money he makes in real estate deals, and all the fancy stuff he does? How many golf courses did he talk about in a day? I don't see why it's arrogant to not believe in Trump as a populist. Or to see irony in the claim that one candidate better cares about, relates to, or understands the poorly educated when his party wants to limit social safety nets, unions, health care, and the ability of poor people and minorities to vote.
As to the left's obliviousness, our candidate get more votes.