See, I just don't get that. To me, Hillary Clinton has a pretty solid middle-class vibe. She comes from the Midwest and spent a good chunk of her adult life in the South. Her early adult life was spent in a little one-bedroom home in Fayetteville. Her career involved actually working for other people, like most of us do. It's a far cry from Trump, who was the child of one of the richest men in America and sent his whole life in a gold-plated jet-setter lifestyle in NYC, as boss of a giant corporation his daddy gave him. So, it's ironic that anyone would point to a "jet set personality" for Clinton, in that context.
Why does Clinton get hurt by having become wealthy late in life, while Trump's silver-spoon existence and billionaire Manhattan lifestyle doesn't rub the same people the wrong way? I think it comes down to hate. Donald Trump hates the same people that the undereducated white working class hates. He hates uppity women, Black people, immigrants, and religious minorities. That hate binds them together. It's the reason that rural Mainer was drawn to him, and why she wound up reaching for an out-and-out lie to explain her vote (because telling the truth, even to herself, would have been uncomfortable). You can't say you picked Trump because he hates the same folks you do, so instead you say it's because Hillary Clinton didn't talk about working people at the convention -- even though she not only demonstrably did, but demonstrably did so far more than Trump did.
To use the old cliche, Trump is the kind of person they'd like to have beer with.... because they can sit around getting drunk and telling bigoted jokes while ranting about "those people." Clinton, by comparison, may share a very similar background to them, but she outgrew that bigoted mindset, and who wants to get a beer with someone who may make you feel bad about being an asshole when you try to tell a nasty joke? I think that's why they call her Shrillary -- the idea that she's the kind of person who'd have the morals to speak out against bigotry, rather than joining in with the "locker room talk."
p.s. The article you referenced was a guest column written by two politically active people from rural Maine, and shouldn’t be presented as an expression of the paper’s opinion
The question is why the paper chose to trumpet that particular view, even when the column contained what they knew to be outright lies, without so much as providing a reality check? I have no problem with them providing a diversity of viewpoints, but when someone is going to make a flat-out incorrect statement about a verifiable matter, the paper has a responsibility to set the record straight. If, for example, I wrote a column saying the Obama years had the highest GDP growth rate in American history, the paper either should require me to remove that flat-out wrong statement before they'll publish, or they should provide, alongside it, an editorial clarification that my statement isn't actually true. If they provide me a soap box for saying wrong things, without correction, then they are shirking their responsibility and they may as well just be Twitter or Facebook.