Error -50 & -69 When trying to sync music Ipod Classic 160gb

Question

Hi everybody,
I recently installed an x64 version of Windows 7 Ultimate. I have an Ipod Classic 160gb (late 2009), and i am trying to sync it to my itunes library. However, everytime i do so, it will copy across a few songs (a different number everytime, no more than 500 though) my Itunes freezes up (as well as the ipod). After a while, once it "comes back to life" i get either "Itunes cannot copy {Song Name} to {Ipod Name} Ipod. An unknown Error Occurred (-50)." or "Itunes cannot copy {Song Name} to {Ipod Name} Ipod. An unknown Error Occurred (-69)".
Here is what i have tried:
Enable Disc Use - No Luck
Uninstall / Reinstall Itunes + Rebuild of Library - No Luck
Uninstall Itunes, reinstall + Rebuild Library on Previous version (9.2) of Itunes - No Luck
Kill APSDaemon.exe While synching - No Luck
KIll all other Apple Services + Processes - No Luck
Uninstall Antivirus - No Luck
Reformat Ipod - No Luck
Create a Virtual x32 environment of Windows 7, and recreate my library using the latest Itunes - No Luck
Virtualize a Mac environment, and try on there - MAC OSX doesn't allow virtualization on a Windows "Base" (what a piece of ****) - SO, no luck
Media Monkey Transfer - freezes up like a dead body, then just crashes.
Manually transfer - Work sometimes, doesn't work otherimes. Seems to be Random.
I know you are all going to say "oh, the song it get stuck on is corrupt". Well, it isn't. The song plays fine in Itunes if i go to investigate. When i go to my music "source" it is an actuall file, with an actual file size. I can also play it with VLC media player as well.
Sync with my Dad's IMAC - Success. My Dad has 5.5gb of music (more than 500 songs). Although Ipod did get seem to get stuck on a couple of songs, it succesfully sync'ed
Use Sharepod - Success (although, i have 2940 folders, and sharepod will only allow me to transfer one folder at a time) - So, No Luck
I know the Ipod is fine because if i Sync via MAC or Sharepod, it will play music fine.Also, before the installation of the x64, it sync'd fine. It would be silly that an Ipod dies because i change my Windows Installation.
Another thing, while in the act of Synching, the IPOD screen displays "Synchronising", then, it will just go to "Connected". On the MAC it stayed as "Synchronising" the entire time.
Basically, i am at my wits end. I have tried everything i can think of.  I now have a very expensive paper weight, which is ******** me to tears.
If anybody has any solutions, or ideas, i would love to hear them.
Thanks,
Lachlan

Answer 1

You seem to have tried everything, and you say it's syncing fine on your Dad's iMac, so I assume, you have also  done a Disk Diagnostic from an earlier post by tt2 and conclude that your iPod Hardisk is good.
You don't have to use it as a heavy paperweight, the problem is only using your Windows 7 machine for syncing.
In your troubleshooting steps, did you try to use another High-Speed USB 2.0 port, USB controller resource are very scarce, so if you use other USB devices, while syncing your iPod, it may just freeze.
Windows have a bad reputation for device conflict, so better don't connect other  USB devices, while syncing, better sync it while disconnected from Internet, stop antivirus just before you go to bed.
Have a nice day!