I thought he was rather crass and generally annoying in his over-indulgent ways. But am not as bothered as a large portion of fandom seems to be at his constant reminding Sam of the deal and that Dean had only one year to live and all that, to me that's big brother taunting little brother just because he can. It doesn't mean Dean is completely unaware of Sam's feelings on the matter, in fact, it *could* be argued that it helps Sam take things a little lighter (not that it works, but it could be part of Dean's intention(?)) since Dean is not all excessively emo on the subject, if Sam's accepts that Dean's accepted it, it might be seen as a step forward from Dean's POV...

I think.