A new mac app has been released called Random Playlist Creator. This application randomly generates iTunes playlists from a source playlist, which can be of any type that references Library tracks.
• Creates multiple iTunes playlists of a specified combined file size or playing time.
• Creates "super-playlists", each consisting of one or more segments (each segment comprises an iTunes playlist). This feature is especially useful for flash-based MP3 players with expansion cards where the internal memory is a different size than the expansion memory.
• Allows the last generated super-playlist to be randomly padded with tracks from previously generated super-playlists.
• Allows groups of tracks to be kept together in a specified order within the generated playlists.
• Provides an enhanced shuffle mode where an entire playlist can be shuffled into a single new playlist with the track groupings intact.