So, the iPod Shuffle should be loaded with a specific playlist, that is played in order, or not. It should NOT be randomly loaded by the host computer. The reason: when you come across a song you really like that's new... YOU CANT SEE WHAT IT IS.
The "autmoatically load the iPod with new songs every time it's connected" feature of the Shuffle isn't enabled with the regular iPods, though. So what I do is this:
1) Make a Smart Playlist, where the song has to be less than 7 minutes, and longer than 2 minutes. This eliminates sound effects, long classical pieces, and Jethro Tull's "Thick as a Brick."
2) Delete everything on the iPod.
3) Go to the playlist, start playing it in random ordeR.
4) Sort by song number.
5) Drag a couple thousand songs to the iPod.
Now, when I hear new music, I can see what I'm playing.
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