IPod (and iTunes) freezes when syncing large playlists

My ipod freezes when updating a large playlist or a lot of new songs. This usually requires me to physically disconnect the dock connector and reconnect the ipod.
If i try to sync the same files using a smaller playlist the ipod is usually able to update.
Anyone else experience this problem and/or have a fix for it?
I've tried resetting/updating software on my ipod with no luck.

Back up all data.
Triple-click anywhere in the line below on this page to select it:
~/Library/Application Support/SyncServices
Right-click or control-click the line and select
Services ▹ Reveal in Finder (or just Reveal)
from the contextual menu.* A folder should open with an item selected. Quit the application if it's running. Move the selected item to the Trash. Relaunch the application and test.
*If you don't see the contextual menu item, copy the selected text to the Clipboard by pressing the key combination  command-C. In the Finder, select
Go ▹ Go to Folder...
from the menu bar and paste into the box that opens by pressing command-V. You won't see what you pasted because a line break is included. Press return.

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    Back up all data.
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