As an avid Science fiction Reader and a long time Role Playing gamer familiar with Time Master, the fact that Sam and Dean did not disappear when Anna returned to the past did not bother me, as there is a theory that when the past is changed there is a short period of time before the wave of change hits when you can go back and prevent the change. I wasn't even to worried about the information John and Mary received changing the future because, I was darn sure that the writer would find a way to erase them, and I was right and what a way it was. What I did not consider and I think you point out so well is that Michael was always behind Anna escape. Now that you said it I am convinced that you are absolutely correct, everything points that way, from Castiel's first meeting with Anna. Wow clever and tricky and now I have to watch the show again.
I wonder if God's End Game for this season is not the apocalypse, which of course this being a show will be averted but showing the angels who have lost their way and their faith a way back to God. Maybe God had not left the building but it is the angels who in losing faith fail to perceive him. Maybe the Winchester Gospels are not for man kind but for Angelic kind. I guess that's actually a little arrogant imagining Sam and Dean as the Messiah for Angels, but it pleases me even so. It also makes an excellent seguay for a story arc for season 6 if it gets renewed and an explanation as to why Castiel would still be around, since Misha has a two season contract.
John thinking Samuel being a heart attack did not bother me, Azazel promised Mary a normal life, two dead stabbed parents is not a great start to a normal life. Samuel and Deanna were dead but I bet a demon of Azazel's power could have altered the evidence. Paying for the hotel rooms didn't bother me, modern money is different but not all the older money is out of circulation, so unless people were deliberately checking dates on the bills between Sam and Dean they could have swung enough money for a hotel room, and rooms were cheaper then too, and credit card fraud was much easier. The evaporating oil and the smudging sigils made sense to me because in previous episodes the angels did not know that the Winchesters and their allies had these things or were prepared to use them, they were arrogant. But Uriel was warned by Anna (who lied) that the Winchester had killed him in the future, and therefore would be more careful and scout the cabin before entering. Anna or he may even had seen the preparations. Your other comments though, I didn't even think of at the time but agree could have been handled better.
And I am all aboard with Team Free Will!! I might need a Team Free Will button or T-Shirt for the March Convention
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Songs in the Key of Supernatural