How can I delete all my music and use iTunes Match?
Q: I want to subscribe to iTunes Match and delete all the music from my iTunes library. Can you tell me the best way to do this?
First of all, I'd strongly recommend keeping the music in your iTunes library somewhere — either on your Mac or within a backup on another drive. I suggest this because there have been many cases where iTunes Match serves files that are poorly mastered or match different tracks (a live version versus a studio version, for example) or bad tracks. You may end up matching your music, deleting it, and finding that you can't get all the tracks you once had (or receive tracks of poorer quality).
Also, there are certain types of tracks that iTunes Match won't match. These are tracks whose quality is too low (below 96 kbps) or are too large (bigger than 200 MB). So, you ideally want to match everything, then find all the tracks that didn't match and save those files. Here's how to do that.
After you've gone through the iTunes Match process — which may take a while, depending on how much music you have — create a smart playlist in iTunes to find the tracks that didn't sync for one reason or another. To do this, choose File > New > Smart Playlist, then set the first condition to iCloud Status is Ineligible. Click the plus (+) button to the right of this line and add another condition: iCloud Status is Local Only (this will find files that haven't yet synced to iCloud). Finally, click the plus button again and add a third condition; iCloud Status is Error. These are tracks that, for some reason, weren't able to sync.
Click OK to save this smart playlist. You'll now be able to, for example, drag all those tracks to a folder in the Finder if you want to save them. Or you can just keep them in your library.
To find all the tracks that are now in the cloud, create a similar smart playlist as I've outlined with the conditions iCloud Status is Matched, iCloud Status is Purchased, and iCloud Status is Uploaded. You can now delete all the tracks in this playlist. All this said, I still recommend keeping a backup, just in case.
How to listen to podcasts from oldest episodes to newest
Q: I'm catching up on some podcasts, and I've been using a Smart Playlist to sync five of the oldest episodes at a time to my iOS devices. The list selects the oldest first, with a limit of five, so I can eventually listen to all the episodes in the order they were created.
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