I’ve been struggling with a problem in iTunes where after deleting files and moving my iTunes library from computer to computer it eventually ends up having several missing songs. The songs still show up in the library but they are missing from the disk. When you go to play the song you get an annoying grey exclamation point and iTunes asks if you’d like to find the song. Eventually I stumbled accross this fix in a comment response to an iTunes rant blog:

In the meantime, here’s the solution I came up with for the multiple dead track issue:

1. Make a smart playlist called “All Files” with this rule: “Artist” is not “123456789″ (or any nonsense name that won’t be in your library).
2. Make a static playlist called “All Live Files”.
3. Make a smart playlist called “Missing Files” with these rules: Match all of the following rules, Playlist is “All Files”, Playlist is not “All Live Files”
4. Select all the files from “All Files” and drag them into “All Live Files”. The dead files marked (!) will not copy over.
5. “Missing Files” will contain all of your dead files. Select all and delete. Voila, a nice clean iTunes library.

I have these three playlists in their own folder. Whenever I gather more than a couple dead tracks for whatever reason, I delete all the tracks in “All Live Files” and repeat steps 4 and 5.

Not as nice as the much needed “Sort by (!)” feature but it works like a charm and it’s pretty simple.

Edit: Another nifty trick is the ability in iTunes 7 and on to run multiple libraries. When launching iTunes hold down the shift (windows) or option (mac) when launching iTunes and it will ask which library you would like to use.

This is nice if you want to keep multiple libraries… like your classical and deathmetal… separate. Combine this with the preferences option to change where the iTunes default folder is (followed by a Consolidate Library command) and iTunes will even move the files around for you if you wanted to keep one library on removable media for example.