You might start with Jerry Kindall's iPod Remix script (www.jerrykindall.com). I've struggled with the same issue with my original 5 GB iPod, used partially as a backup drive, and a collection of over 6 GB of songs.
iTunes allows you to limit a smart playlist to a total size
where you get 'Limit to 25 songs' by deafult change it to 'Limit to 30 GB' and select by random
by Tilo R Oakes on Jan 14 | 10:21 am
The problem with your solution, Tilo, is that Mike wants to limit a collection of playlists to 30 GB.
by on Jan 14 | 12:01 pm
Well, Mike, your ultimate solution was just released and posted today to VersionTracker: Playlist Blender, $10 shareware from William Wareham. Check it out.
You might start with Jerry Kindall's iPod Remix script (www.jerrykindall.com). I've struggled with the same issue with my original 5 GB iPod, used partially as a backup drive, and a collection of over 6 GB of songs.