Trouble importing music from extenal HD

I have a large music collection on an external hd consisting of about 400gb that I'm trying to import into itunes. I made a new itunes library, located on my external hd, by going into preferences/advanced, and changed the location of the library and imported 120 gb of music without any problems.
Then, while I as importing music, I recieved the message "Attempting to copy to the disk "my hd" failed. The disk could not be read from or written to."
After this itunes would not import any more music. Eventually I found that if I went in to preferences/advanced, and unchecked the "copy music to itunes music folder" options, itunes would import my music just fine.
This I can except, although it is a little more labor intensive, except a second problem started. When I would go to play some of the music I had recently imported, I get the exclamation point beside the track and the message "the song xxx could not be used because the original file could not be found. Would you like to locate it."
I understand what this means but itunes seems to be doing this randomly to different tracks on different cds. This means once i import music to itunes, I may have to do it 2-4 times before the link to the file actually stays in itunes which is completely unmanigable with a collection of this size.
I have been able to import files into itunes a second time, after the file was disconnected from itunes, and it has stayed in itunes successfully. This makes me think it is an itunes problem and not something to do with the specific files that are being disconnected.
I know it's a lot of info but any suggestions would be helpful.
I'm a little frustrated.
Thanks

Are you using a USB external drive? I've had problems like that before, trying to move large chunks of data, especially music, with USB. If you have the option of using Firewire with that HD, it works a lot better.

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