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