Unable to transfer Songs to Ipod or Flashdrive etc

I have about 66gb of mp3s on an external firewire drive,
and have recently purchased an ipod, however, about five percent of my mp3s won't transfer over to my ipod despite playing fine in itunes and quicktime.
When I try to copy them onto either my ipod or (my old usb flashdrive mp3 player) my computer freezes. This has been a problem for a while now and has become really frustrating since purchasing the ipod (30gb video).
There seems to be no way to predict which songs will be a problem as some songs on the same album are fine while others are not.
Any suggestions would be appreciated (other than the usual "get a newer computer").

A few extra details. The mp3s have been ripped from cd and are not in mp2. The problem is not playing them on the ipod but transfering them. This doesn't seem to be a problem transfering them between computers with firewire but when transfering from HD to a usb device like the ipod or a usb drive (whether it is an mp3 player or just a usb flash drive with only storage capacities).

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