Personally - I think Scott Adams is more than a little bit batshit insane, but I certainly don't think he's punching down in the strips presented here.
I transitioned at work, and I've tried really hard not to be this character. I asked people to use my new name and pronouns but never complained to HR if they didn't. I made an effort to be as friendly and hardworking as possible, so that my conservative coworkers wouldn't see me through the lens of the "culture wars" like this that they're fed. This kind of comic was the stereotype I faced.
It worked for me. I changed peoples' minds, got respect for being reliable no matter my looks, and eventually started passing so nobody remembers I'm trans anymore.
Exactly, so by presenting in a particular way, you were able to get people to use the pronouns you wanted. I think this is the key to why people find pronoun declaration so meaningless — pronouns are meant as a shortcut chosen by the speaker to refer to another person based on who that person appears to be. Making pronouns into a declaration breaks a fundamental piece of language functionality for very little gain.
Dilbert works by personifying roles. It doesn't do much in the way of role subtext.
Those policies aren't coming from the peers.
It's how Dilbert is every engineer, PHB is every clueless boss, and Wally is every elder peer, Asok is every junior peer. That's what makes the comic relatable. It also, as the article points out, what provides constraints to these characters as well.
If it was mocking HR policy, then it would be signified with Catbert. It's not. It's very simple.