I do not understand.
So, from the moment I started college, and first owned a computer, my music collection has been largely digital. I can keep CDs organized like nobody's business. But files? That's a different story.
It's been incredibly disorganized for the last couple of years, and has really needed attention. So I had my parents ship the external hard drive to Chicago, and finally sat down to sort things out. What motivated this? My iPod stopped showing up in iTunes a while back. I haven't been able to add new music since Novemberish. It was starting to be a problem.
It was an overwhelming process, which turned out to be easier than I expected. A couple of days later, I'm done. I don't even think I have a lot of duplicate tracks lying around. So I'm all set to restore the little bugger of an iPod that isn't behaving, and lo and behold.
There it is. In iTunes. Pretending it's been there the whole time.
Sometimes technology amazes me.