I might be completely off with my thoughts, but I'll still share. To me, it seems that your T has some unresolved issues himself surrounding certain topics that tend to come up in your therapy and maybe that is why the "why do I do certain things" cannot be addressed.

Take the recent incident with the emails as an example. I can in some way understand both sides of this issue. On the one hand, I'd probably have fears similar to yours, that suddenly in-person sessions fall away and so on. On the other hand, I would probably be bothered by constant check-ins if I were Dr. T. For you as the client it's in a way important to hear that something like this can be annoying. It's probably something you struggle with in other areas of life as well and being told how you make others feel is useful. You can only start change if you realize there is a problem, so being made aware of such things is good. However, in your therapy it often seems to stop there. Which I think stems from the fact that he doesn't fully understand how and why it affects him the way he does, so a) he can't tell you why it might bother somebody, just that it does, and b) he doesn't seem to be able to look past his own emotions.

Let's for a moment imagine he was fully aware of his part in this. Say, his mom was very controlling and always checked in on him multiple times a day and he has come to terms with the fact that this makes him more jumpy, and he has learned to distance himself from his mom. In this case, I think when he got bothered, he could first analyse whether it stems from his own stuff. He then could say that yes, it does affect him more because of his story, but even so such checkins are bothersome at some point and boundaries can be established. He'd then bring it up to you, explain how other people might react when they constantly get such emails and lead you to discuss why you even feel the need and different skills that will help you without having to check the session is still happening (as well as similar things with others). At no point would it be "I am annoyed by the constant emails" and more "such emails can be annoying, we should work on you relying less on them".

What instead seems to happen is that he becomes aware of his emotions, but doesn't actually really know why they happen or how it affects your work. It's not "oh, a reminder of my mom again, okay, it's not LTs fault, but there's stuff there that we should work on" and instead he gets reminded of his mom without even knowing, projects parts on you and doesn't realize, tells you that it's annoying and doesn't want to really go any further because he doesn't fully understand his own reaction.

It kind of reminds me of the story with the stone. There, he didn't seem aware of either the fact that people use transitional objects or that he wouldn't like the idea of it being a reminder of him to you. If he did understand those two factors, he could have either said "I'm not comfortable with it" before giving the stone and establish a boundary, or thought to himself okay, this is one of my issues, but people do this all the time, let's try it and see how it goes for her. Instead, he only realized his emotions after the fact and didn't seem to have any awareness of how to handle it.