Constant Lockup with Ipod Sync

Just to let you know before I explain my problem:
I am using Itunes 5.0 (although the problem happened in 4.9 too)
I have used the "restore" option multiple times to reset my ipod.
I have run a disk check on the ipod from debug menus
I am using a USB 2.0 connection.
I have an Ipod Photo 30gb
I am using Windows XP SP1
Whenever I try to put music onto my Ipod using automatic or manual update, disk mode or not, itunes locks up completely anywhere between 5-10 songs into copying. It doesnt matter what songs i'm copying, and no specific song is the culprit.
After itunes locks up, interestingly enough, I can neither end task on itunes nor restart by conventional means. When I choose start>shutdown>restart, it is inable to end itunes and just hangs. I have to hard reset it by flicking the power switch.
I recently tried syncing contacts from outlook. This instead gives me "The IPOD cannot be updated. An unknown error occured (-50)"
I have tried defragging my disk, reinstalling Itunes, restoring my ipod.
Anyone have any suggestions?

I have a similar problem with my iPod however the max I've ever got to is 8 songs. I've looked alot into this as it's really frustrating because my iPod was an Xmas present I was really excited about. I still have no solution to the problem however I have found out that it's not the iPod it's iTunes. Not much help I know, but it's something

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