I can't update my songs

I have had this big issue with my ipod for a while. About a month or so I guess it started. My sister downloaded a new itunes to my computer. I had to re-put all my songs in. So I update the iPod to get all my songs again and the new ones I added. Rather then update it gave me a warning saying it can't update it because it could not read the disk which was titled under my ipod's name.
then I tryed restoring it, it worked for a little bit then it said something caused it to be unable to restore and it gave me some number along with the error. The first time that month ago I experienced it, I figured I needed to put my iPod CD in to re install it or something. Then when I finally found it this friday, I attatched my iPod to charge. It also added the original songs I wanted to update into it. I assumed the problem was fixed but it's starting to do all that again.
Should I just put the CD in and re install everything or is this something thats wrong with the iPod? PLEASE Help! It's bad enough that the iPod is also having re-charging issues probably sue to the battery.

Well, now when you try to restore, what's the error message that you're getting?
CG

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