There's something... dissonant... about putting gwern on trial and deliberating on whether he's guilty of second-degree shitheadedness

That'd be another point missed. I am not interested in a ritual condemnation of gwern, or advocating for it (or chastising you for failing to advocate for it). I am a bit confused at what exactly your standards are, such that the behavior described (do you feel my description is inaccurate?) doesn't get to be fairly described in such terms.

It doesn't sound like the right question to ask;

Then why did you ask it, and answer in the negative, by stating Gwern hadn't done anything horrible? Isn't that intrinsically subjective? Why the need to defend the behavior as something no reasonable person could take issue with? That's what I'm getting at here.

But since that is not to be, what are we supposed to do?

Not go out of your way to absolve him of it either? This isn't like, a ravening mob with pitchforks and torches calling for Gwern's blood. Your options are not limited to a choice between offering sanctuary and tossing him to the wolves, and it's kind of scary that you appear to view it that way.