I finally had to buy me an IPOD (Nano) and its one of the best investments Ive made since I work out alot but I can tell you I do not like iTunes. For one as soon as I plugged in my Nano iTunes started automatically tranferring my music library to the Ipod which I didnt like because I wanted to select which music I wanted on there. The worst thing though (and Ive found this to be not ucommon) is that iTunes kept crashing and my computer would restart during song transfers. It would transfer about a dozen or so songs and then reboot. Finally I went searching for alternatives and found out that Winamp offers a plugin that syncs with your IPOD. However I could never get it to recognize mine. Finally I buckled down and bough a program called anapod. What I like about it is it allows you to copy and paste your selection to your IPOD. After I shelled out $25 for the program I found out there are other free alternatives that I wish I wouldve tried before spending money but it was worth the investment.

Hmm i liked itunes on windows, and juk on linux, but i dont have windoz anymore and have never had in iopd i just thought it organised music well.
But there is a feature that stops the automatic trnasfer of music when you plug the ipod in. And also i wasnt aware that there was a natice linux version of itunes, so WINEing it make be the reasns for the crashes.
I dont own an ipod, but my friends do, and none of them use itunes on linux. there are open-source alternatives to it i cant remember xactly which but i think Amarok may have an ipod feature,
have a look around sf.net for a free and good alternative.
And unlucky bout buying it first lol there is almost all the time a decent open-source alternative to fairly basic programmes for linux

Ryan

google gtkpod. it's a pretty good itunes replacement for linux