Itunes Crashed when uploading library To Classic IPOD

Not too sure if anyone else is having this problem.But i have updated the itunes and ipod software, and have reset it and also restored it numerous times.
But every time i connect my ipod and either manually sync my music or whether it does it automatically it will get to around 150 songs and then will crash and will sometimes get different errors.
Does anyone have any ideas on what could be causing this or even better some possible fixes?
Cheers

Jeremy,
Thank You for the reply but my issue was not in the attachment you sent.
iTunes freezes when I attempt to add music to my ipod classic especially playlists I have made.
iTunes recognizes my ipod but when I "add" that when the issue starts.
I have my large library on a pc using windows 7. I have no issue adding music to my device on
my macbook pro but like I said, my 60,000 song plus library is on my pc.
Any additional help would be greatly appreciated.
Happy Holidays,
JJ

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    iTunes freezes when I attempt to add music to my ipod classic especially playlists I have made.
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