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My digital music collection has long surpassed my archaic, third-generation, 20GB iPod’s capacity.  Conveniently, iTunes recognizes this fact and offers to only sync a selection of my music for me.  The problem is that iTunes always seems to pick the same songs every time I sync… meaning that any new songs I’ve added usually don’t get included.  Thankfully, you can sync from any playlist you’ve got, and it turns out that iTunes Smart Playlists allow you to do some really clever things.

So then, my requirements for my “iPod Selection” playlist:

1. All of my newest music is synced.
2. The rest of the space is filled with a random selection from my whole library of music.
3. Only music is synced… no podcasts.

Turns out this was not hard to do at all, and with only three Smart Playlists I had exactly what I wanted.  Read on to see how it’s done…

First, create an “All Songs” playlist that lists only your music.  This means everything that is audio but NOT a podcast.  You may want to add additional rules here to exclude audiobooks, comedy, or other things you don’t want.

Next, create a “Most Recently Added” playlist which will show the last 200 songs you added to your iTunes library.  You may want to increase or decrease the 200 item limit depending on how many new songs you normally have.  On a good month I add anywhere from 50 to 100 songs, so 200 is a good number for me.

Finally, we put it all together with one more playlist, “iPod Selection”, which pulls from both of the above lists and limits the size to whatever will fit on your iPod.  In my case, it’s around 18.5 GB, but you have to use a whole number, so I had to round down to 18.  I’m not sure if it includes ALL of my new songs, but in the few tests I did it seemed to pick up most of them.

Now you’ve got your playlist, so you just have to tell iTunes to use it when syncing.  Hook up your iPod and click on it in iTunes to pull up the settings menu, then choose the Selected Playlists radio button and check your iPod Selection playlist.  Sync and enjoy!