Do you have any better luck with that if you update to iTunes 10.6.1.7?
From the notes for the release:
iTunes 10.6.1 provides a number of improvements, including:
• Fixes several issues that may cause iTunes to unexpectedly quit while playing videos, changing artwork size in Grid view and syncing photos to devices.
• Addresses an issue where some iTunes interface elements are incorrectly described by VoiceOver and WindowEyes.
• Fixes a problem where iTunes may become unresponsive while syncing iPod nano or iPod shuffle.
• Resolves an ordering problem while browsing TV episodes in your iTunes library on Apple TV.