" For example pretending that the issue is seeing generic genitals without regard to sex - that was pretty blatant rationalization, which in a less fraught conversation he likely would not want to stand behind."
While I appreciate your attempt to see the good, I think you're wrong here. Note, Jared makes his assertion that women "can easily ignore a penis if it's not erect and being poked in their face" in his very first comment. The conversation wasn't fraught. There *was* no conversation at that point. I think he's standing behind this claim because he simply doesn't care about women's rights or boundaries.
As for holding his feet to the fire on specific points, that's a useful tactic if you're engaged with somebody who is genuinely interested in thinking about an issue. But Jared's arguments were so trivially idiotic that it's clear he was either unwilling or unable to consider any perspective that didn't make it as easy as possible for people with penises to enter women's spaces. Regardless of the implications to their safety and comfort. As you say, this isn't unprecedented when somebody is desperate to defend a pre-determined position. But in those cases, it's next to impossible to get them to think clearly, in real-time, during conversation on the internet.
Sometimes, when I'm debating someone particularly unreasonable, my focus isn't really on changing their mind. Or, at least not on making them admit they were wrong at that moment. The odds of that happening online are vanishingly small. Instead, I'm working through the logic in the hope of planting seeds in their mind that might bear fruit later. And also for other readers. My conversation with Jared has been read by hundreds of people on Medium. It's more for their sake that I'm working through the points. I don't think anything I said would have made Jared acknowledge the flaws in his arguments, even though I find it very hard to believe he didn't see them. Indeed, whenever I made a point that he couldn't refute, he just ignored it and moved on.
So yes, I think Jared is concerned with protecting trans people, who are indeed a vulnerable population. I'm concerned with protecting them too. I'm simply not willing to unilaterally trample over the rights of *another* vulnerable population in order to do so. Compromise is required on both sides of this debate. There is no solution that will make everybody 100% happy. But it's the utter disdain for women's rights and boundaries that I found not just "irritating" but downright disgusting.