Yeah - when she appeared in the dream sequence, she was very standoff-ish and Dean was (understandably) embarrassed about her presence. She seemed very snooty.

The no free will thing actually jives with angels, since (biblically) they aren't supposed to have much free will anyways. That's was Lucifer's biggest problem, if I recall.

Besides, Michael acts like he is actually in touch with God, like he is crystal clear on what he has to do next and not bound up in all the "Well I guess God is dead so we might as well start paradise like he wanted" tangle like all the other angels. Is there a chance that Michael knows how to contact him? Could Dean saying yes mean that he finally gets a way to learn God's location?