An article at the Electronic Frontier Foundation reports that RIAA (and various co-conspirators in digital content industries) ultimately want to take away your right to ANY copying of CDs that you have purchased for any reason.

They even had the profound gall in their February 2 DMCA Ruling Joint Reply Comments assert that it is illegal to make a copy of a CD you own just for backup purposes. What alternate solution do they present? Why, to just buy another copy of course! From page 40: "Even if CDs do become damaged, replacements are readily available at affordable prices." That's right, you can just simply shell out another $10-$20 (even though you have already done so for the original copy) to continue to use the music you have already paid for.

Pages 21-22 of the same document make it clear that the RIAA also does not necessarily condone copying music from your own CDs to your iPods, because it is "not established that space-shifting or platform-shifting is a noninfringing use.”

Whatever.  

In an otherwise good review of the new 1GB iPod nano, Digit's Dan Frakes laments the absence of the Autofill feature for iPod minis and nanos. This feature, which is available to shuffle users, automatically syncs the iPod with songs selected from the user's library or a specific playlist. (It assumes that the library is larger than the iPod will hold at one time.)

iTunes' Smart Playlist feature is a very powerful way to reproduce this feature for other iPods. I recommend that all iPod users play around with it to see what it can do. (I'm not providing instructions, because it's so easy to use.)

I have a playlist very similar to the autofill feature (though my iPod is larger). I found that random listening after a while resulted in having some songs that had been played several times, and other songs that had never been played. To resolve this, I created a Smart Playlist called "100 played songs". The inclusion criteria, not surprisingly, are (a) it is 100 songs long, and (b) the Play Count is zero. Randomly selecting songs is also an option. After I play some songs in this playlist and sync my iPod, those that I played are removed (since their Play Count is now "1" instead of "0"), and they are replaced with other unplayed songs.

Eventually, I played all songs in my library. When that happened, I adjusted the playlist so that it selected songs whose Play Count is "1", which selected from a much larger pool, as you might imagine. This is a great way to not only fill smaller iPods with randomly selected songs, but also to hear songs that you haven't heard in a while.