I hear your frustration Albadross and, completely understandable, desire to get your point across.
People are very wary of engaging, particularly around work, because transactivists’ modus operandi is to attack. And, although, there are transpeople with whom you can definitely talk (i.e. some on here), they do seem fairly thin on the ground.
His ‘over sharing’ might be tempting you as well. Maybe you can sense a need and you want to provide something. Which, of course, is lovely of you, but it does make you vulnerable.
Maybe sleep on it for a day or two? Sometimes these things become clearer after a little distance.
Either way, I would make up my mind to only talk very superficially.
Also, I’m a little wary of needy people. It’s quite hard to extricate yourself once you’re committed.