Songs won't update.  Error message "can not be read from or written to"

Right, so maybe someone can help me.
I've had my Nano since Christmas and have never encountered any problems with it until recently.
Whenever I try and update my iPod (or my husband's for that matter) I get the error message: Attempting to copy to the disk "Gatsby" (name of my iPod) failed. The disk could not be read from or written to"
Sometimes one or two songs will work, and then I'll get the message. If I try again another few songs will work and I'll get the message again.
I have tried everything I can think of.
I have tried resetting my iPod. I've tried reinstalling iPod Updater and iTunes. I've tried restarting the computer. I've tried restoring the iPod to factory settings. And I still have the same problem.
I tried calling Apple Support but they weren't able to help me much. So maybe someone here has an idea. PLEASE HELP!
Since I've restored the iPod I no longer have any songs on it. I only have the few that have managed to copy inbetween attempted updates. My poor little iPod is useless until I can fix this problem.
I have iTunes v6.0.4 and iPod Updater v1.1.1 (the update from 2006-03-23)
Please help!
Thanks!
iMac G5 1.8GHz PowerPC   Mac OS X (10.4.6)  

Well, I know my operating system is up to date. I know iTunes is up to date. I know iPod Updater is up to date.
I don't think it's a damaged music file, because it doesn't hang on one certain song. It manages to update a few, then I get the error, if I try and update again, it does a few more songs then I get the error again. I've updated dozens of times with the same selection of songs and I've never had a problem.
I tried resetting the iPod. I tried restoring it.
Still hasn't helped.
Someone suggested using fsck from my terminal, but it came back saying everything appeared to be okay. But, my songs are all on my external hard drive, does that make a difference?
It's never seemed to matter before.
I don't know what else to try.
I don't think it's a problem with the iPod itself. My husband's iPod is doing the same thing, which makes me wonder if it isn't my computer, or perhaps a problem with iTunes or the iPod Updater.
I've tried using a different cable, and different ports, but I still have the same problem.
Any ideas?

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