I finally got to see SPN 8.14 and figure that it was worth suffering through the first half of the season for. In the episode around Valentine's Day over the last few seasons, Dean has given Sam something, usually a heart, even though it's been passed off as a bad pun. This time, Dean gave something that means more and probably cost him more than almost anything he's given Sam except the deal for his soul. It was given as a response to Dean really hearing Sam say he had faith in him and asking for faith in return. It happened quickly. So fast that it's hard to get a cap that isn't blurry.
Along with paper, Dean handed Sam his trust, faith in his ability to do these trials and survive them, and hope that what Sam says about the light at the end of the tunnel is true. It is a recognition that his Prime Directive - look out for Sammy - has changed. I hope it's stepping away from a suicide mission. To me, it's like knighting your squire and sending him off to do the great deeds that you aspired to and being willing to let him lead you into battle. Dean just put his life and Sam's into Sam's hand. Fortunately, it's a strong hand.