In iTunes, when you delete a song it used to ask me if you would like to move the song to the trash. Now that option isn't there, and I want it to come back.
I'm sure what I did was click "no" and checked the "don't ask me this again"... but in fact, I do want it to keep asking me. I frequently add/delete songs, and I don't want the unwanted music to clutter my music folder.
I was just messing around, after backing all my music up of course :headphone , and I clicked "Consolidate Library"... now when I go to delete a song the option is back. Yay.
I think it might have something to do with the music being located in the "iTunes" folder you specify in the iTunes prefs.
My other music was stuff I had imported from vinyl, and I imported it into another folder. I figgered it out.
And yes, it does have to do with tracks being in the library designated in iTunes. Mine will ask me the question for tracks I know are not stored in my designated library folder, but it will not delete those tracks even if I click yes. It will only delete tracks stored inside the designated Library folder.