I personally loathe ipods, both the unit, and itunes.
Out of all the mp3 players I've used/spent significant time with - iriver, ipod, iaudio iwhatthehellsiwthputtingiinfrontofeverything, sony, creative zen, archos and one or two more I've forgotten the winners are
cowon iaudio, hands down.
They sound the best (close fight with a couple of sonys though; one discontinued model is actually better imo, but it would be pointless to bore you with that), battery lasts about 60 hours of play time on their standard mp3players, interface with a pc is exactly as though it were a memory stick (I am so never buying an mp3 player that needs any software ever again); you just plug it in and drag and drop, they play most formats (mines a little old now and only wont play mp4 - plays flac and vorbis and the like no bother), has a usefull EQ and other toneshaping kit. Theres no competition really; ipods are a toy by comparison.