Freezing when passing the songs from iTunes to iPod

After I bought the 60gb video iPod I had a problem to send the music from my iTunes. If I use the automatic method, the transfer freezes after 200 or 300 songs were transfered. If I use the manual method and copy groups of 200 songs each it will go until the end of my 5.000 songs.
I would prefer to keep the automatic updating.
Any idea of how to solve this problem?
Thank you.

I have resigned myself to try to set iTunes to manual sync - at least until the initial collection has been transferred. It will take a while, and I am sure that once done the world will be right again, the clouds will part and the angels will weep. Until then however, I'm wondering if it was worth the upgrade since my old iPod (3g 20gb) would sync just fine on FW.
The question still remains (in my feeeble mind) why Apple would "degrade" the iPod capability to use only USB - a technology which has never (again in my mind) worked properly and by that I mean up to spec.
Aren't you suppose to be able to connect over 100 devices to a single USB chain? Heck, I can't get more than a couple devices connected (using self powered USB hubs of course) before things start to fail.

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