The latter! He's from before the big showdown with Dick. I figured, for the set up of the game, it only made sense to take him from this period, or from when he was homeless and human in S9. Every other point, I just didn't see him checking out no matter how low he was feeling. And of the two, I always felt like they never quite did enough with this Cas. Also, I definitely approve of the hug life! They BOTH need it! Hurt/comfort ftw!
I'm glad you're looking at Reconsider for it! :D I've been hoping for a Dean - especially a later seasons Dean! I think Cas needs someone to help him focus if he's to really develop, and I REALLY wanted to see how different canonpoints would change their interactions. Are you grabbing him from the very end of the episode? Because POOR DEAN, coming from THAT to find this Cas waiting for him!