Syncing iPod Classic (120gb) to Windows 8

Hello,

I recently got my hands on an iPod Classic and can't for the live of me get it to fully sync with my Acer Aspire V5 with Windows 8. I have an iPod Touch that I was able to sync just fine when I bouth the computer last fall, but I needed an iPod with more space so I got this used iPod Classic. I have tried *so* many things to get it to work, including restoring it several times, reinstalling iTunes and making sure the iPod software was updated.

I just restored it again and I'll walk you through what happens, this is basically what has happened to me more than a dozen times.

-I plug it in (I've tried multiple cords) and Windows tells me there's an error on the disc. I follow the steps to repair it, it says it's repaired.

-I do the first sync with iTunes. I select to sync music (not even going to tackle audiobooks yet) and it begins to sync the 2117 songs.

-Somewhere between 320-370 songs, it gets hung up on a song and basically freezes for a bit. Then I start to get error messages. It never freezes on the same song so I know it's not the song. And most of my songs were imported by CD or bought through iTunes so I know they're the right format (plus they synced to my iPod Touch just fine).

Error dialog box #1: Attempting to copy the disk "(disc name)" failed. The disk is not available.

Error dialog box #2: iTunes could not copy "(song name" to the iPod "(disc name)" because an unknown error occurred (-53).

-So then I eject the iPod, unplug, reconnect and try syncing again. It usually doesn't sync any songs at this point. It won't sync anything else until I restore it again.

Help please! I'm so beyond frustrated. The help documents have not provided any advance toward a solution and phone support charges.