Problems transfering music from external hard drive to ipod.

When I plug both ipod and external hard driver (WD 1600B014) into my Gateway laptop, only 1 device will work at a time with the other saying "usb device not recognised". This means I am unable to copy selected itunes songs onto my ipod.
This is driving me insane as I have 60gb of music on my hard drive which I want to chop and change frequently.
I have tried all manner of solutions including buying a powered usb hub (belkin) and starting a clean sheet with my laptop, installing all manner of new drivers for the usb ports.
I have the same problem with my 5G ipod 40gb.
I have tried the same problem on my dads desktop computer and the same problem arrises.
Does anyone have any answers as this has been driving me mad for ages and ages.
Is this a common thing or is it a problem with Western digital hard drives (although i thought they were a pretty big brand).
Any help would really be appreciated.

if I want to copy all those song files onto my iPod, they have to be copied into itunes first, and there's not nearly enough space on my desktop for that.
No, you don't have to copy the tracks to your internal hard drive. Just turn off the "copy music to iTunes Music Folder when adding" option in the iTunes Advanced preferences. Then use the "Add To Library" menu command and select the appropriate folder(s) on your external drive. iTunes will add the tracks to the Library but not move them to the internal drive.
Once that's done, use iTunes to transfer the music to the iPod. You can then, if iTunes is set for manual synchronization, remove the tracks from the Library if you want to remove the reference to the external drive.

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