Music fails to copy to iPod Video - Urgent help needed!

Recently i done a stupid thing with my iPod, i done a defrag on it using windows utility. Though i have done it before, no problems. I have though just been told that its a bad thing to do.
After that, itunes did not recognise my ipod (iPod Video), i then restored it using V1.11 firmware, then went onto iTunes to upload all my music, it goes so far (say the first 300 out of 4550 or a number below 300) then stays on random track, then the iPod disconnects. Since then i have used previous versions of the firmware (1.0, 1.1), still does the same thing.
Can anyone help, cause i now live in spain (europe), since moved from scotland. It would be a pain to send it back if its not bust.
Oh yea, my music is all stored on a external western digital HD, connection is a 2.0 USB. Had it for 6 months or so and had no problems with it so far.

Generation 1 vs generation 2 has zero impact on using Enhanced Session Mode to copy files in and out.
Under the hood, Enhanced Session Mode uses RDP. So, the RDP stars must align for the file copy to work. This can be impacted by group policy, improper RDP settings, the VM not being Windows 8.1 or Server 2012 R2 or higher.
http://technet.microsoft.com/en-us/library/dn282274.aspx
Brian Ehlert
http://ITProctology.blogspot.com
Learn. Apply. Repeat.
no settings in group policy.
all other things were identical.
i removed that VM & created new one, since there was no solution to that. maybe a bug.
thank you anyway

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