iTunes Music Folder inside iTunes Library

You're welcome. 🙂

Looking good from what I can see. Yes, you should be able to sync your devices with selected playlists. If that doesn't give the expected results try iTunes > Preferences > Devices > Reset Sync History.

tt2

See Make a split library portable - Apple Community for some background. Typically on a Mac your iTunes library would be stored at ~/Music/iTunes with media inside ~/Music/iTunes/iTunes Media. iTunes Music is the old name for the media folder. You appear to have the components of your library scattered around somewhat. In a modern library (post iTunes 8) the album artist folders would normally be inside a folder called Music which is inside the media folder so that the media folder has sections for each media type.

Quite how you would proceed from here depends a bit on how large the media collection is and how much free space you have. When discarding duplicates you also need to make certain which files the library is connected to.

tt2

Hi,

I'm not entirely sure I have the whole picture of your library but I think I see enough. Backup first.

The key database file is the one called iTunes Library in your second screenshot. The normal location for this would be ~/Music/iTunes where ~ is your user folder.

1. With iTunes closed you can move the four files that you see in that screenshot into ~/Music/iTunes
2. Move the folder called Album Artwork that is in the same folder as those files into ~/Music/iTunes
3. Rename the file iTunes Library to iTunes Library.itl
4. Press and hold down option as you start iTunes and keep holding until asked to choose or create a library.
5. Click choose, then browse to and open ~/Music/iTunes/iTunes Library.itl.
6. Check that your music still plays as it should.
7. Go into iTunes > Preferences > Advanced and reset the media folder so it becomes ~/Music/iTunes/iTunes Media
8. Use the menu option File > Library > Organize Library, tick the boxes Consolidate Files and Reorganize Files
9. Click OK and leave iTunes to copy all of your media into the new media folder.
10. Test the library, backup the iTunes folder, clean up the original copies of files outside of the iTunes folder, check things still work after cleaning up and emptying the trash.

In the unlikely event that things stop working after a step please stop and come back for advice. Make sure you know exactly what action you took just before things went wrong. Having made a backup at the outset you can always get back to that state if required.

tt2

At a guess 2013 is likely when you moved your library from one computer to another, or at the very least opted to consolidate the library. Consolidating will look at every track connected to the library. If the current path is outside of the designated media folder, and the file exists at that path, iTunes makes a fresh copy inside the media folder, updates the reference in the library, and thereafter ignores the original file. Where are your most recent additions stored? Do you think there are any orphans, i.e. files on your computer that aren't connected to the library, or is the case that you have duplicates in the file system, but not in the library.

What about the size of the library and the free space? If you have enough room I will suggest steps to get the library into the standard shape of an iTunes folder, containing an iTunes Media, which in turn contains all of the media of the library, and how you can clean up the remaining duplicates once that has been done.

tt2

Select the tracks of the album you want to be in the artist's folder and press CMD+i to get Song Info. Untick the compilation checkbox and click OK to apply. Make sure that album artist and/or artist are consistent across the album.

tt2