Help copying files from iTunes to external hard drive

I have a bunch of music files (about 15,000 of them) that I want to back up to an external hard drive. They are only files of a certain bit rate, so I can't just locate them in a particular folder and copy them; I need to sort them in iTunes and copy them from there. I tried to highlight all of them and just copy them, but I got the spinning wheel for a couple minutes and then the operation stopped. I then figured out that I could transfer about 1,000 at a time -- I got the tracks by bands starting with A, then B, then C, to transfer. But now I am stuck. When I try to transfer files now, when I highlight them in iTunes, the window showing the destination folder on the external hard drive disappears, and I can't transfer them. Before, it seemed like both windows were active, but now they are not. Anyone know the solution to this?

The Windows drive is probably formatted NTFS which is not natively writable
by the Mac. It should be formatted as FAT32 to be usable on both.
Dave

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