If there's a gradual shift in the polls, I'm not sure what that would mean. Which scenario did you have in mind?
I have a feeling that polling is used now a political weapon not a measure of reality.
Unlikely, considering there's one every other day
(that's actually not the best method to evaluate him, because he provides estimates of chances and could be better evaluated with something like the https://en.wikipedia.org/wiki/Brier_score that checks for calibration as well, but it's more intuitive).
538 didn't fail to read data properly re Trump's nomination. Trump was a new phenomenon with no history to build a model from. 538's mistake was guessing instead of admitting they had insufficient data -- which is bad behavior, but not because their preferred methodology is bad.