Dan and Tom can speak to this, but by my reading of the guidelines, "criticism of the current administration" and "views on topics like gender" are both explicitly prohibited:

"Please don't use Hacker News for political or ideological battle. It tramples curiosity." (https://news.ycombinator.com/newsguidelines.html)

It has nothing to do with being on the side of "the opposition" or "the man," it's because those sorts of posts inevitably lead to the same, repetitive, off-topic debates and flame wars.

Flagging should be used as a cudgel against posts that break the rules. There are plenty of places on the internet to debate politics and gender; HN is not one of them.