User Centered

Through trial and error, I've discovered that iTunes will only "Keep my music organized" if I do things...just...so. (note, this is the version that came installed on my wife's mac. Possibly old and possibly bug-fixed by now).

iTunes let me name tracks as the CD was being imported. Usability principle: Accommodate the user's desired task order. Well Done, Steve. So I figured it would Do The Right Thing in regards to filenames. If the system needed to import to some temporary file, that's fine, just make sure that you (the system) change the filename when you (the system) do have track information (from the user).

Nope.

If you name a track before the import of that track begins, it will be saved with the correct filename. If you name a track after a track is imported. Ha ha! All Will Be Lost(tm) and it will magically revert to "Track 1" the next time you start iTunes.

The principle here is that the underlying system state, filename = track name or filename != track name, is invisible to the user. To the user, changing the track name is changing the filename. Therefore, it's the system's responsibility to ensure displayed information matches the underlying system state at all times.