Easy first. The "random" in title means the smart playlist will limit, say 25 songs, in the playlist, based on "random". In iTunes, everything works fine. But when syncing it to iOS device, that playlist just truncates first 25 songs (assume that smart playlist will filter more than 25 songs based on conditions) and display them, not the one showed in iTunes. I want to use this feature to discover my library and listen to something new everyday, until I go through the entire library.