Ares
Well Cas really didn't outwit Crowley, I mean even Crowley doesn't break a deal and he is a demon. No one would really expect an angel to do so. I still think it is safe to say the Crowley is still cleverer.
I'd say he outwitted Crowley; he surrendered the dog blood to Crowley, who assumed it was legitimate. Castiel had screwed him over already, I don't see why he'd assume he wouldn't here.
Ares
But the god storyline... Yeah, that's going to be ridiculous regardless what happens.
You can expect that old!God will be involved.