Q: Is there anyway I can shuffle through songs on iTunes without the songs being checked? My iPod only holds 400 songs so my iTunes only plays these songs which gets quite boring after a while.
A: One of the disadvantages to managing your iPod using the “Sync only checked items” setting is exactly what you describe: Unchecked items are skipped during playback in iTunes unless they are specifically selected for playback.
The best way to avoid this problem is to leave all of your tracks checked, and then create playlists to sync with your iPod. This not only allows you to playback all of the tracks in your library properly, but the use of playlists can provide much more flexibility for loading content onto your iPod, particularly through the use of “Smart Playlists,” which can be used to automatically select certain content for synchronization based on specific search criteria. For example, a Smart Playlist could be created to select 1 GB of music from the “Rock” category that is rated three stars or more and that you haven’t listened to in at least one week.
Setting up your iPod to sync selected playlists is actually quite simple. Once you’ve created the playlists containing the content you want on your iPod, simply connect your iPod, and then select it from the source list where it appears in iTunes on the left-hand side of the screen.
Once you’ve selected your iPod, the main screen should show a summary of your iPod configuration, and several tabs across the top. Simply select the “Music” tab and you will see a list of synchronization options:
Choose “Selected Playlists” and then simply check the individual playlists that you would like synchronized to your iPod, and then click the “Apply” button. Those playlists and all of the tracks in them will then be transferred to your iPod.
Once you have this set up, you can then re-check all of the music in your iTunes library so that it again plays properly when listening to your library through iTunes. A fast way to do this is to simply select the “Music” category from the top of the iTunes source list, and then hold down the CTRL key (Windows) or CMD key (Mac) while clicking on an empty check box—this will toggle the checked status of ALL displayed tracks simultaneously.