Ah, but we're not talking about high end sound quality are we? We're talking about whether they are obsolete. I know that I'm not going to exercise with my netbook under my arm, or drive around with my laptop connected to my car system,etc.......
There are many, many users of IPod and the like over at the headphone forums that have made it an art wrestling the best sound out of these units by modification and tweaking. I think they might disagree with you. I've heard more headphone rigs that use a portable music player as a source that sound WAY better than many hi-fi rigs I've had the pleasure of hearing, including some of those "high-end" ones at RMAF and such. Just don't use mp3 rips on it and use the damn line out, not the headphone jack.
I hate Winamp. It's a PITA to get set up like you want and everytime I look it's trying to upgrade on me, changes my layout when I accidentally click the wrong spot, frustrating as hell. I prefer Foobar or Quuxplaey over Winamp anyday. Winamp seems to be for people who like to make fancy visual presentations of their player.
If I had the programming ability I'd never use a Microsoft product again. Their platforms suck and have more bugs than a $2 hotel.