Q: I periodically like to clean out my iTunes library, in a major way. However, I make myself nervous: will I delete something I want to retrieve at a later time? Is there an automated, or at least easy, way to backup files before I delete them?
A: Actually, we’ve recently gone through a similar cleaning-out process, and we really enjoyed the ease and safety with which we went about it. Here’s our process:
Create a new empty, standard playlist, and call it “Marked for Deletion.”
Create a smart playlist, with the single condition that “Playlist is not ‘Marked for Deletion’”. Call this playlist “Working List.”
Now, enter the “Working List” playlist, and as you progress through it, drag songs into the “Marked for Deletion” playlist. They will subsequently disappear from view, as if they were actually deleted. This allows you to see the results of your cleaning efforts, while keeping them 100% reversible: to “undelete” a song, simply delete it from “Marked for Deletion.”
Keep working through your “Working List,” make changes as necessary, and when you’re ready, open your “Marked for Deletion” playlist, and burn it to a Data CD or DVD using the procedures in our tutorial here.
Then, simply delete the “Marked for Deletion” playlist and all songs it contains by selecting it in the Source column, holding down the Shift (PC) or Option (Mac) key, and pressing Delete.
We’ve found this to be a fool-proof, easy, elegant way to conduct a massive overhaul of our iTunes Library, and we highly recommend it.