What can I do about an error (-69)?

I'm so frustrated!

I added a song to iTunes a night previous to this incident, but I did not sync my iPod at that time. I also updated iTunes that same night.

Later the next day, I plugged in my iPod and I got an error screen on iTunes. It said the iPod was corrupted. I have delt with that before, so it didn't seem like a big deal. I ejected the iPod and to my horror EVERYTHING on my iPod was gone. I did not restore or reset the iPod, I simply ejected it after deciding to sync it later. I've tried re-installing iTunes/repairing iTunes. I even re-installed Quicktime. I have also restored my iPod many times since.

Nothing seems to be working. I don't feel any of my music files are damaged and I don't want to go though unchecking and checking boxes for 11,000+ songs only to not have some of those songs on my iPod. Is there anything I can do to get my iPod working like it was? It is a 160GB iPod Classic. I also have an 80GB Classic which I tried syncing with iTunes with little success.

As of today, I downgraded iTunes to 10.7 and it seems to be helping but I keep getting this error.

Edit: Before I installed the older version of iTunes, I also got the error message; "iPod cannot be synced duplicate file name was specified."