I don't think you should leave your T. I actually think that was a good, honest response to what you told him. I think that he said quite a few of good affirming things in there, but you focused on the part where he said he needs to get comfortable with transference...implying he isn't already comfortable. And I can totally understand that...because I do the same thing...focus on the kind of negative remark in all of the positive.

I wouldn't avoid talking to him about transference. He always said he wasn't experienced at it...and I don't know how you can be comfortable with something you don't know a whole lot about...BUT he is willing to learn more and get comfortable with it. So I would say keep doing what you are doing and explain it to him over and over if you need to.