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Vermont is fairly Conservative. Not as conservative as southern states certainly, but they have voted Republicans as their leaders for many years. Then they switched to Democrats, then it was a mix. but in general it has been Republican.
They are in a sort of bizarre spectrum (the center is probably not the right word). The people of Vermont are pro gay rights, but then are also pro gun (90% of the people in Vermont own guns).
He isn't a Democrat, but he does Caucus with them. Also he is a true liberal which is what the Democratic party supposedly is, so he should win the Democrats. In terms of having a chance to win, Hillary with this email scandal is going down in all polls. Many Americans are critical of her and are tired of establishment politics so she probably won't win the democratic nomination because democrats know she can't win.
As for the rest, refer to my response to Metarch.
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