Itunes freezes when trying to transfer songs to ipod

I attempted to sync my ipod to my itunes and it was going fine for the first 3000something songs and then itunes froze for a while, along with the rest of my comptuer. It wouldn't even allow me to force quit the program. After a few minutes, an error message popped up telling me that there was an error in attempting to coping my songs to the ipod and then it said "(-69)". I've tried to drag the songs on manually and in chunks. I thought it might have been a specific song that was messing up the transfer, so I didn't add the song at which the transfer stopped, but this didn't help.
Does anyone have any suggestions? my itunes did something similar (freezing for a bit and error message) when it says it's "determining gapless playback."
Thank you.

Hate when that happens. Just follow the steps in this article and it should fix it.
Good Luck,
Rachyl
http://docs.info.apple.com/article.html?artnum=302684

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