Guys - Thanks for the quick responses!
I don't currently have any iPod, but I'm wanting to pick one up after the holidays. I have my files stored on a PC and I don't use iTunes. Worse! I don't even have access to highspeed internet where I live

I currently have the music stored on my hard drive, and backed up to a USB2 portable hard drive. I store all my music files in folders titled by artist, then album title, with each song titled in the folder. I know I won't get it all onto the iPod, not even close. But I know one thing: I sure don't want to think about going back to (and being limited by) a 6-disc changer!
Mike