Itunes with 10.3x not transferring large files to external hard drive

I have been unable to transfer any large files, basically anything over over two artists or so from old external hard drive for my old windows xp computer to my new external hard drive (both iomega and western digital have been tried) without the transfer cutting out and popping up a message to effect of itunes can not copy or add file to folder...something like that. am i missing something that i need to be doing? ive got about 33,000 items, and the thought of doing them 10-15 at a time really isn't something i want to do. But as of this point, i can't find a way to simply xfer the whole itunes library from the old external to the new one. Thanks for any help.

You can transfer purchased content ONLY! Unfortunately, you have no choice as to what gets transferred. Here are some work arounds
1. Delete off iPod Touch/iPhone/iPod then transfer
2. Transfer all content then delete from computer

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