LT, I think the most important factors in your expressing concern and anxiety about your therapist's well-being are being lost. I don't think the useful consideration is about the nature of human caring or where the focus of the therapy is flowing or whether he is annoyed or whether clients can comment on a therapist's life, etc. These sound like distractions to me and in that sense they do take the work away from being about you.

For me, the therapeutic work here would be about the interpersonal interactions in the relationship e.g. what are my projections here? Is my concern for his well-being actually an expression of concern for my own well-being? If I think he is struggling, am I actually the one who is struggling?

Similarly, the intrapersonal dynamic is potentially being highlighted for you. Are there aspects of your self who are worried that you are going to let yourself down? Is your inner critic questioning your mother self? These are guesses of course, but the conflict and concern which is showing itself in the relationship could be a reflection of your inner conflict and concern.

It doesn't sound like he treats your anxieties and concerns as information which both of you can use to help you understand your internal world. He sounds stuck in an anxiety-reassurance loop with you which isn't working for you - mostly because he can't even reassure you sufficiently. I think identifying patterns or being aware of replays (such as the ex-MC stuff or parental relationships) goes some way to explaining the familiarity of your anxieties, but it doesn't sound like it is deep enough to really help you get inside those feelings and find a new course for yourself.

This is a very long winded way for me to say that I get the impression that he repeatedly misses important information and opportunities.