New iTunes Library Organization: Suggestions, Problems, and Solutions

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iTunes version 9 has a much needed new feature to help clean up the clutter that has built up as Apple added successive new features and functionality to iTunes. In previous versions, musical artists had folders that sat along side container folders for Movies and TV Shows.  This made for a messy folder, and those of us with just the right (wrong?) touch of OCD found it maddening.


But under iTunes 9, you can select "File" --> "Library" --> "Organize Library ..." and choose to "Upgrade to iTunes Media Organization".  This will consolidate all you musical artists under a "Music" folder and leave a clean "iTunes Music" folder.  In my case, only seven folders are now housed in my "iTunes Music" folder:

• Automatically Add to iTunes (more on the new watch folder later)
• Downloads
• Mobile Applications
• Movies
• Music
• Podcasts
• TV Shows

Ah!  Much organization agony released!  Now, if the parent folder was not called "iTunes Music" ...  But I guess they need to save some improvements for version 10 (I mean besides a 64-bit Cocoa rewrite, of course).

I did run into one problem, and there may still be other issues.  After iTunes claimed it was finished with the reorganization of my library, I still had hundreds of individual music artist folders that were not in their proper new home of "Music".  This was driving me nuts, because the option was grayed out, so I could not re-run the "upgrade" (reorganization).

It turns out iTunes moved all the actual music files were properly moved, but iTunes left behind litter in the form of "artwork.jpg" files under many of the album folders and kept the album and artist folders to hold them.  (I'm assuming these files were created by third party used to find album art.)  Once I realized it was not the music files, I cleaned out the artwork.jpg files and their surrounding folders, and everything seems right with the world.

Update:  So, it looks like the reorganization process is basically working, but it is leaving files and folders behind, if it does not know what to do with them.  Anything not mentioned in the Library database, any miscellaneous graphics, and any enclosing folders for said unexpected files.  All left behind in their original cluttered locations.  I guess I understand what is happening, but I wish Apple had included an option to automatically remove the remnants into a folder.  Manually cleaning up after the upgrade/reorganization is a boring pain.