Some thoughts:
this is as a said a very non-Christian universe, however nominally Christian supernatural is. (If the mythology is hoodoo, that makes a lot of sense.) A lot of the gray comes from that. And apparently applies to Angels and Demons, not just people and monsters. A lot of life and afterlife is navigating arbitrary and unfair rules, and defying them or finding ways around them.
A thought about Ana: her timing was unfortunate. She spend millenia just watching, then chose to fall just as the war heated up. As a really big mojo angel, deserting in the heat of battle, that probably made what she did worse.
I was amused at the fact that after Dean was twice chided for confusing reality with porn, his reality
becomes
porn.
But Ruby retains her demon powers, and Anna had to abandon her Grace.
Always struck me that God is a real stickler for rules. Angels were made without free will, end of story, you know?
he apparently hadn't earned the enmity of as many (and as powerful) demons as Dean had, so he may not have been given the same sort of personal attention and fast-tracked for demonhood.
Also, they made deals with different demons, yes? John sold himself to the YED, Dean sold himself to the red-eyed variety.
As a really big mojo angel
Given that she said she was Castiel and Uriel's boss, I really want to know if/where they're going to pin her in the existing Christian angel pantheon.
Isn't Uriel an archangel? Or is that just Michael, Raphael and Gabriel?
(Who would be the 4th Angel who has seen the face of God?)
Uriel is an archangel, depending on what part of the Bible you ask.
I'm wondering if one of the four is Lucifer. (Morningstar, don't ya know...)
The face of God makes me think of the Face of Boe.
Hmm, John Barrowman on SPN. . .