I've never understood this "poor sound" argument.
Firstly, you're playing mp3s - it's gonna sound rubbish. Secondly, it's a portable music player - why the hell would anyone care (within reason) about sound quality? People adjust to whatever they hear within seconds. They sound absolutely fine. I listen to music off my phone when I'm out and about, it sounds terrible, but who cares.
Even if they sounded rubbish, the interface and speed of the things would still make them the best. Itunes is great, and the way the ipods work is lovely. The touch is a bit gimmicky for my liking, but the nano and the classic are great.
I would consider waiting for the next gen of solid state mp3 players, which will surely be touching 100gb. No reason they shouldn't last for ever...
Also, about the whole mac hating thing, grow up.