ITunes displaying error message when trying to copy songs to iPod

I've been having intermittent problems with my iTunes/iPod setup since about the time I got an iPhone 3G. The problems were with syncing or not mounting correctly.
I'm still having the mounting issues but I'm no longer able to sync my contacts at all (I don't sync anything else). I manually add/remove tracks from the iPod, but can also no longer do this.
I have also tried resetting the iPod and restoring through iTunes. With the restore option I receive the same 'insufficient privileges' warning and it will not restore.
I have also recently upgraded to 10.5.7 (and repaired permissions before and after).
I'm fairly sure it's the iTunes setup on my current machine as when I use the iPod on my iMac I can easily add/remove items.
I'm tempting to use the restore function from the iMac but am skeptical it will work because the only thing new introduced to the MacBook is the iPhone. The iPhone syncs bookmarks, contacts, some photos, applications and that's it.
Anyone have some theories? I've read some places about the iPhoto cache being a problem but I deleted it and I'm still having the above issues. Boo.
Thanks.

Try this. When the stick is mounted on your desktop, right click "Get Info" and at the bottom choose "ignore ownership on this drive." See if that works.
Bryan

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