IPod Touch 3rd Gen will not sync or charge

Hello all,
I'm using a 3rd gen ipod touch, but when I attempt to charge or sync this device the ipod refuses to respond. I've upgraded itunes to the latest version, and I've also ensured I'm using a working USB 2.0 port. When the iPod is detected, I can go to device manager I see that the device is plugged in. Despite all of this, the ipod doesn't appear in itunes and is never charged.
What gives?

I've gotten the iPod to sync after restoring it and not changing ANY of the music sync settings.  I didn't even click "sync music", I just have it on manual and clicked autofill. 
After it synced all of the music successfully, I tried to sync a playlist (my recently added), and it's gone bonkers again, it won't sync the playlist's music, or any new music now. 

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