ITunes keeps borking my iPod! HELP!

Question

Hello all. First time poster here. I desperately need some help!
I'm not entirely sure what kind of iPod I have, but it's a 30GB video that I was given by my girlfriend back in '05. Not sure what generation that is. I recently downloaded iTunes 9.0.1.8 for Windows XP, and when I docked my iPod to add some songs to my iPod, it gave me the message of "Itunes cannot read the content of the iPod "DAVE'S IPOD". Go to the Summary tab in iPod preferences and click Restore to restore this iPod back to factory settings." This originally happened a few days ago, and I ended up having to put it in disk mode because it kept endlessly resetting itself. To get it to stop, I had to Disk Mode it, and then restore the Pod to factory settings. From there, I had to completely resync my entire iPod. Today, I went to load new music onto the iPod and it gave me the exact same error message. I've deleted and re-installed iTunes, I've stopped and restarted the iPod service in computer management..nothing has worked. It never did this before this new iTunes, and I'll be absolutely honest when I say that I'm really angry with this. I've searched Google for the answers for others, but no one seems to have a precise answer. I'm well out of warranty, so taking it in for fixing/buying a new one would be rather expensive and in this economy, that's out of the question.
If anyone can help, please do. My iPod is a integral part of my everyday life, so losing it is pretty rough. It still plays all of the old music that's on there since my last re-sync a few days ago just fine, so I know the music is on there.
Thanks!

Answer 1

Maybe, I can't tell from here ; ) It's not normal to have 30 instances of one band/folder.
So maybe it's my first suggestion - something bad in your library is causing the iPod to error when it syncs.
Do you have those multiple instances of Linkin Park in your itunes library, and also PC's hard drive? (my guess is yes) Or does it just get duplicated on the ipod? (never heard of that)
You can try building a new library. Syncing it to your gf's itunes a few times without getting the error would also narrow down whether it is your library or the ipod.
If you want to try running CHKDSK, it's in the Windows helps or easily googled, and I linked to the stuff about reinstalling the USB drivers.
My advice is to try syncing it to another itunes library. The results there would tell more about whether it's an iPod or PC/iTunes problem.