Itunes freezes when syncing songs (-69)

Whenever I go to synch my 16GB iPod Classic, it keeps freezing on certain songs and tells me there has been an unknown error (-69). However these songs have played fine on both my iTunes and my iPod before, so they shouldn't be corrupt. Even tracks I've brought from the Store have this problem as well as those i've imported on CD. I've followed Apples Support page suggestions but I'm still having problems.
Any suggestions?
I should note that all my music is stored on an external hard drive including my iTunes folder.

Hello Smythe,
Thanks for using Apple Support Communities.
Please follow the steps in the article linked to below to resolve this issue of iTunes becoming unresponsive when an iOS device is plugged in.
iTunes: May become unresponsive when connecting iPhone, iPad, or iPod touch
http://support.apple.com/kb/TS3219
Take care,
Alex H.

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Back up all data.
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~/Library/Application Support/SyncServices
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*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...
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Compaq Evo N800c
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Track 5, start time 10:24:57
Track 6, start time 14:16:27
Track 7, start time 18:34:26
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Track 9, start time 23:27:57
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Track 12, start time 35:51:63
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Track 14, start time 44:55:44
Track 15, start time 50:42:60
Track 16, start time 54:38:39
Track 17, start time 57:44:22
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Itunes freezes when syncing songs (-69)

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