Whats the difference between Shuffle and Random playback order modes?
Random mode picks tracks randomly, without special measures to prevent track repetitions other than a simple check to prevent the same track from playing twice in a row. Shuffle modes keep an internal randomized list of tracks in your playlist and play tracks according to their order in that list, so you don’t get repetitions until all tracks in your playlist have been played. Shuffle’s randomized track lists for each playlist are re-created on foobar2000 restart or when starting/advancing playback with another shuffle mode. Note that manually selecting a track to play in your playlist will result in shuffle playback continuing from that track’s location on the randomized list, which is often perceived as repetitions: each time you manually choose a track to play (by doubleclicking it in playlist, etc.), shuffle plays the same tracks after that track; use ‘Play → Random’ menu command or the ‘Random’ button when you want to continue playback from a random track instead.