Ok, I've struggled for the longest time on deleting songs from my iTunes library. In the past I've simply hit the delete button after highlighting the song and then watched it disappear. I never received the "Move to Recycle Bin" pop-up message and so consequently, the file was still being stored in its respective location (in my case, the G:/Music folder). It was like just hiding my dirty clothes under my bed for the rest of eternity. Not that smart.
So, for those of you who would like a clear answer on how to permanently delete files from iTunes, instead of hiding them under your bed, try this...
*First of all, I'm gonna say that this will only work if your music collection is conveniently located in one folder, i.e., G:/Music.
1. Rename your music folder to "iTunes"
2. Click on Edit > Preferences > Advanced. Under the iTunes Music Folder destination, click "Change" and add the new "iTunes" folder where all your music is located.
3. Now your music library will have to be re-assigned to the correct folder destination. I just deleted my entire library (keeping all files on my computer) and then added my new destination folder.
Now, anytime you try to delete a song from your iTunes library, it should ask if you wish to keep the file or move it to the Recycling Bin. This should also work for highlighting multiple files at the same time.
Annoying, but it works.
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