MASIMO,
I have been thinking about you.
How long of a notice did he give you that he was retiring and then traveling for six months?
How long did he give you to process this with him...before he retired?
You may not want to hear this but it's possible he didn't give you enough notice. It would have been better if he had decided what post-therapy was supposed to look like...and talked about this with you for many sessions..
I agree, if he would discuss some kind of boundary now..at least you wouldn't feel like you are flailing around.

I don't blame you for emailing him again to ask him to discuss/negotiate post-therapy boundaries. Please don't be hard on yourself. He should have settled this with you months ago.