This article said that it involved quite a bit of direct personal pressure and that his reversal was pivotal (but it may not be very accurate). 

I only saw this now - huge kudos to Kontsevich for being so clear-eyed about this.

Basically I'd bet capable people are still around, only that the circumstances don't allow them to rise to the top for whatever reason. 

My guess would be that nowadays many people who could bring a fresh perspective, or simply high-caliber original thinking, get either selected out/drowned out or are pushed through social and financial incentives to align there thinking towards more "mainstream" views.

I wasn't quite happy with the OPs phrasing it in terms of dom/sub dynamics, but couldn't quite put a finger on it - I think your point that it's more about social expectations and connections in general captures it pretty well!

Your dig against pick-up artists as it's stated doesn't seem to amount to much more than "these guys feel icky", which is most likely just reflecting it being low status. (There's also separately a bunch of toxic behavior related to the pick-up mindset one could rightfully criticize.)

I did not know this! And it's quite an update for me regarding Mochizuki's credibility on the matter.

This seems like nonsense. If there's any way to formalize what Mochizuki claims, he could and should do this to achieve what might be the greatest intellectual upset in history. On the other hand, he's likely just wrong about something and his proof wouldn't go through, so there's no use in trying to settle this with a proof assistant. 

I'm always wondering whether there's something going on here, where - by definition - we can rationally understand how high-value a utopia would be, but since we can't really tell for sure where things will end up, we may be assigning a way to high intuitive probability to it. 

It feels like your implicitly framing is that one should welcome technological progress and be active about adapting to it, but I'm lacking the perspective that one (sometimes) should be active about shaping the course of progress itself. 

Also, most of the time people who are seriously discussing a matter likely don't talk about whether a technology is good or bad as a whole, but refer to the way it's currently being realized in the world, so that seems like a strawman.