Dean's reaction to his official death in Skin is interesting. Actually, it's his lack of reaction that's interesting. He expresses no concern about the loss of his identity. He doesn't seem to be concerned that his father or any of the Winchester colleagues, so to speak, will hear about his "death" and be concerned. His one comment is, "How many chances am I gonna have to see my own funeral?" It's flippant and casual--amused even--and in sharp contrast to the look on his face when he stared at the dead shapeshifter earlier.
The other half of Dean's attitude can be seen in the beginning of this episode, in his conversation with Sam over Sam's emails. Dean seems genuinely surprised that Sam is bothering to keep in touch with his college friends. Sam is keeping his ties to his "normal" world, laying groundwork to come back to that someday. Dean...doesn't get it. Which is not a new revelation; one of the first things we learned about the Winchester brothers back in the pilot was that Sam wants to be normal, and Dean thinks that's both ridiculous and unrealistic.
Shapeshifter!Dean would have you believe Dean is jealous of Sam's shot at normalcy, and wants it for himself. I think he puts the unreliable in unreliable narrator at that point; he knows enough to know what will make Sam squirm, plus I think he's garnishing Dean's issues with a heaping helping of projection. The shapeshifter thinks of himself as a freak, wants a normal life. If the download he gets from Dean tells him otherwise, he might not be able to believe it.
I think that, for Dean, drivers' licenses are for other people, you know? The loss of your official identity is the kind of thing people with houses and W-2s and college friends worry about. Dean's got monsters, girls in tight shorts, and his family to think about, not whether his Social Security Number has been deactivated. Even at the end of the ep, he apologizes to Sam for the way his life has changed, and says he wishes it could be different--but just for Sam. He doesn't say anything about wanting something different for himself.
Makes you wonder what will happen if Dean lives long enough for all that to catch up with him, doesn't it?