I would be concerned that he is being too directive. My understanding of transference is that it is best observed by the T, but interpretations regarding it need to be carefully timed according to client "readiness." And the resolution of the transference is a latter phase of therapy.

I guess I would wonder about the T's confidence that he feels the need to keep bringing it up. And I don't understand why he is disclosing so much. That's a separate issue. I guess I don't understand his focus on the relationship aside from transference, either. I mean, if he needs to keep bringing it up to assess his own understanding, that seems odd to me.