I’ve got an iPod that can’t store all my music, but I still automatically update checked items in my iTunes library (it’s a syncing option). I’ve found a workaround for one of my wishes that Apple probably won’t be adding any time soon. My desire is to sort tracks by check mark box (whether selected or unselected). There is no way to do this natively, but we can configure a smart playlist.
Make a smart playlist by holding SHIFT, and clicking on the button on the bottom left. It looks like a gear or cog when SHIFT is held down, and it’s a plus sign (+) otherwise. You should see a popup to set rules and options for the play list.
Edit the settings to match the picture shown. Uncheck “Match following rule.” Check the following three check-boxes, and edit the second check box so your entire library is considered. There are several ways to catch all of your items, but this works if your library is less than 900GB.
Now you’ve got a playlist of all of your checked items only (I called it “Checked on iPod”). Anytime you uncheck an item, it will instantly leave that playlist; and anytime you check an unchecked item, it’ll hop into this playlist.
You can have a playlist of all unchecked items by making another smart playlist. This time all we is do match the following criteria (leave this option ticked), don’t limit items, don’t match checked items, but do live update. Make one rule that the… Playlist / is not / playlist of checked items (name of the playlist we just made).
The end is result is two playlists that show what is and isn’t on an iPod if the settings sync only checked items to your iPod.