Targeting specific counties in safe states is beyond stupid.
normally yes but it is an act of symbolism. If Orange County becomes winnable to the democrats, it is a way for the democrats to assert themselves that they are truly the dominant national party the same way that the party was from 1932-1968.
But you've got it backwards. If the Democrats regained their position (say through a realignment) results like this would be a symptom of the change rather that its catalyst. The Democrats winning VT is one such situation. The factors that turned Vermont from solid R to solid D were a part of something larger. Symbolic victories don't make the change, no one really cares in the general public, it's just the end result.