Software is up to date, but can't sync music on my 3rd gen iPod.

Before I begin, I wanna clarify... my iTunes software is up to date, and I've turned my computer on & off to help resolve this.
Last night, for the first time, I couldn't sync one music purchase on my iPod. The sync would complete, but my song never appeared on my iPod. During that same sync attempt, a message popped up claiming that 2 of my OLDER songs couldn't be synced because "an error occurred." Never happened before with those songs or other music purchases! Also tried clicking on transferring purchases just in case that was the issue. My new song never appeared.
Then today, when I went to try again the whole sync stopped. Up popped an error message with a big red "X" saying my iPod couldn't be synced. Wth is going on- any ideas? Help!

daughter of isis wrote:
Tried both resetting and restoring. As predicted, the restoration process wiped out all my music. When I went to re-sync, everything returned except one old Napster song from a couple years ago...and ALL the songs I've purchased on iTunes are GONE. Poof. Now it's worse.
You must have blinked when you got to this part of my post - "make sure you have backups of all of your music"

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