I've got a first generation iPod bought on the first day they were offered for sale that's been in use nearly every day for my metro commute and it's yet to even hiccup. I have gone through two sets of earphones though.
Buddy got a new pc version (40gig model...using it to transfer files as well as play music) and it also has performed flawlessly and integrated painlessly with his system. The iPod (and iTunes) has made him put aside his absolute hatred of anything Apple.
It's an amazing little device....