Updating iPod hangs iTunes

I have a laptop that I use on a docking station at home and at the office. My iTunes library is on an external hard drive at home, and I play songs directly off my 60GB video iPod at work.
This setup has worked fine in the past, but I have recently been having some issues connecting my iPod at work. The "Updating iPod" message appears, and the spinning activity icon appears next to my iPod in the left-hand menus. It works fine for a while, but soon the spinning icon stops and iTunes freezes. I can CtrlAltDelete out of iTunes but that is it.
I have tried the 5 Rs (short of re-formatting the iPod since I don't really think that is the issue!) but am a loss as to what to do next. Any ideas?
Gateway M-685E Windows XP Pro
Gateway M-685E Windows XP Pro

Hey, you the man. I just want to say thank you. I hooked up a just repaired touch wheel iPod to my son's g4 iMAC, and it kept hanging on random songs and even the one's it transferred, it did slowly. I tried everything everyone else has, I did restores and erases forever. And it kept hanging up, so I had to frequently disconnect the iPod to get control back of the computer. This morning I was on the phone with Apple tech for over an hour. His conclusion was that because some of the songs weren't purchased from the Apple Store, I needed to manually transfer each song one at a time. I had to go, so didn't get to try it until later today and same problem. Again I called Apple tech support. Guy was very nice, on phone with him for 90 minutes, he didn't think the first advice made much sense. He gave up in frustration when we couldn't get into the disk utility because iPod kept going to automatic update. He told me to call back tomorrow and speak to a specialist. He said he's never had this much difficulty with an iPod. After the call, I managed to get into the disk utillity and do the erase and repair but didn't do anything. When I finally deactivated the auto update, manually transferring the songs one at a time didn't solve the problem. I read your post, started up after disconnecting the iSight firewire cable, took a chance of activating auto update of songs again, and voila, it transferred all the songs (all 176 of them) in about 10 seconds, like a warm knife through butter. And as they said on Saturday Night Live, it felt "like butter." I will call Apple tomorrow and tell them they really need to do something about this. In the meantime, I'll keep iSight disconnected whenever songs are being transferred into the iPod.
Again, your advice is much appreciated. Thank you for the post.
Steve
Mac OS X (10.4.3)
Mac OS 9.2.x

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