I like iPods for their compatibility. iTunes, iPod, hook it up, drag and drop and done.
Anything outside, most likey have to use a player that you don’t use to archive or like to use with an mp3 player you got. My second choice would be Zune, but would have to make sure I can buy mp3 from the Zune marketplace and free of DRM.
I like just a straight mp3 player that plays music and video, no games. If I ever found myself wanting to play a game, I would get a PSP or Nin. DS.
Hoping my next phone will be an iPhone or something like it.