Just about everyone that uses iTunes has a hella hard time keeping their music files organized. This is a shame because (a) it’s actually pretty simple and (b) it is a colossal pain in the ass to move your library if it’s not organized correctly. (Note that I’m talking about the organization of your actual music files and not the appropriate tagging and categorization of your music library.) The bummer of the thing is that the folks at Apple unwittingly made this more complicated and difficult by trying to make it simple and easy. It happens. Trust me. I have been building software for just over a decade now and it happens all.the.time. Don’t get mad at Apple for this one. Let’s just fix it.
First I’ll tell you what you need to do, and then I’ll explain why.