Q: Will I EVER be able to shuffle playlists on my iPod? Or is there any way to get the iPod to shuffle playlists?
A: As demonstrated by the release of the iPod shuffle, Apple seems to love shuffle features, so who knows what the future holds? As of today, however, you can’t directly shuffle playlists, either on the iPod or with iTunes, but there is a way to get around this. The iPod lets you choose whether you want to shuffle by song or by album (Settings > Shuffle). If you want to shuffle a playlist in its entirety, you can set Shuffle to Albums, then change the album tags of all its songs to My Album 1, or anything you want. Do this for all the playlists you want to shuffle. Of course, you’ll no longer have the real album name, but you may not care about losing that in the file tags.