Everything you just said is dead on. Man, if you’re ever in Atlanta, let me buy you a beer (or three).
On your frustrations with certainty in writing, I’ve been thinking a lot about that as well recently, and I think it’s not just a function of human inclination, it’s also a function of the business of chasing clicks. Particularly secondary sharing. The highest traffic activity on places like Facebook is arguing, and the weapons people use in arguments are media chunks that either proclaim “You’re Wrong!” or “I’m Virtuous!” Those are the weapons of culture wars. Since those are the most useful in the argument, they get shared the most. And if it’s a group argument, then members in the group grab the weapon and use it somewhere else.
So the shift towards certainty in media is tied at the hip to how much money you make from secondary traffic. And this is going on everywhere. Medium is a microcosm of individuals subconsciously exploring this, but the media at large is a macrocosm of businesses who are spending time and money behind the scenes intentionally capitalizing on it.