Warning: Spoiler Alert
BOBBY!! BOBBY!! BOBBY!! Oh, Bobby!! It was really nice to see him again, and especially nice to see him kick Sam's ass for not trying to find Dean when he was stuck in Purgatory. Sam completely deserved having Bobby telling him that he was a dumbass, cuz he really should have tried to find his brother (regardless of what the supposed agreement was, cuz that's what they do ... and he had no idea of knowing whether or not Dean was stuck in Hell ... again).
Also, speaking of Bobby, I'm not sure why it is that Dean was so surprised that Bobby was in Hell, just cuz he was one of the "good guys". Regardless of what kind of person he was, did he not remember that year that Bobby spent in a wheelchair ... and the deal he made with Crowley so that he could start using his legs again? It wouldn't matter what kind of person that Bobby was, or if he "deserved" being able to make it into Heaven, cuz of the deal that he made, he would have taken the escalator down. And being someone who was so very important to the Winchesters, Crowley would have been even more unwilling to let him out of his deal. It probably would have made him extra happy to know that he had someone so important to them somewhere where he could torture him.
But now he's in Heaven, and I kind of want to believe that Ash is going to find him, and he's going to be able to hang out at the Roadhouse of Ash's Heaven with Ash and Pamela. That would be fun. And maybe Bobby would even be able to find out if John ever managed to make his way up there after he escaped from Hell at the end of season two.
And Naomi helping Bobby make it into Heaven after Crowley was trying to make sure that he was drug back to Hell ... I really don't trust her, not after what all she was doing to Cas. And of course, she tried to make it look like Cas was completely nuts for thinking that she was trying to make him do something that he wouldn't have done normally. She just can't find out where Cas is, and she thinks that she can find him when/if Cas tries to contact the boys again (which I'm not sure that he will this season. Next season, however, he probably will, since he's supposed to be a series regular again).
I really think that someone needs to be with Kevin more often than any of them are, and they need to be far more worried about him than they are. All of this translating is really doing a number on him, and I don't think that it's going to be much longer until the poor boy burns out. It makes me wonder why the boys don't wonder why Chuck didn't have this same sort of reaction to being a prophet, since they are all supposed to be human, and Kevin is having such a bad reaction to the whole ordeal. I have become convinced that Chuck is Metatron, so there would be a reason for why he didn't go completely bonkers (cuz he was already a spiritual being by the time that the boys met him), but Kevin is still a human kid.
What with Naomi making her way into the boat that he was holed up in, it kind of makes me wonder why the boys didn't take him to their new secret clubhouse. At least then, he would be able to have someone looking after him pretty regularly (since Garth always seems to be away when the boys come to check on Kevin (since the boy who plays Garth is on another show now)) ... and he would be able to have a bit of his own space (since their clubhouse seems to be rather large) ... and he would probably be safe there (since the place would have been ransacked ages ago if there weren't things there to ward off anyone who they wouldn't want to come waltzing in whenever they felt like it.
Oh, and also, Benny!! I am sad to see him go, since there was so much more that they could have done with him, but maybe he did what it was that the writers wanted him to do (in that he changed Dean enough to make him see that not all "monsters" are non-humans, and some humans are monsters). But that doesn't mean that I woulnd't have liked him to keep running around and helping the boys, since that would have been awesome, and he tried so hard to get himself out of Purgatory. But maybe he was getting tired of trying to be good and not eat people. At least he was able to change Sam's mind about him before the end. That's something, right?