Itunes Freezing On Mac Os X Tiger


Okay, I resently tried reformating my iPod to work with windows because I wanted to see if I could use my iPod with both my Window's PC and my iBook. After being disappointed I decided to restore my iPod with the latest Mac Version so it would only work with my iBook again, now when I tried to transfer all my songs to my iPod, iTunes would freeze right away. I can transfer small amounts of my music manually to my iPod, but I would still like to know why this is occuring. Here is my set up:

Window's PC running XP

ibook running Mac OS 10.4 Tiger

iPod is 3rd Gerneration (touch buttons) with firewire cable

iTunes is the latest update

My music is stored on an external usb harddrive, brand new harddrive installed in it