re: Liberal/Academic elites using "sort of"

While I'm not in the proximity of academia, I can imagine how this habit could become common in liberal arts classes where professors solicit varied opinions and interpretations.

Your example of the beheading is a little extreme and not good usage... unless the professor was intentionally aiming for humor through understatement and you missed the joke. Otherwise, a professor using "sort of", "kind of", "in a way", "I see your point, but... " or similar expressions to acknowledge that a student has a point but perhaps not the whole picture isn't unreasonable.

I suspect you'd find less of this in classes like physics.

TLDR: It isn't the worst habit if a discussion/conversation is intentionally open ended and seeking perspectives. I can see, though, once options are laid out and if the situation calls for decisiveness, it may come off a bit milquetoast-like if a person persists speaking this way.