Quote:

Also uselful would be a 'don't play again in random mode if played less than <adjustable> songs ago.
Often if you have a fairly short playlist on random, it will play the same song a few times before you hear every song in the list


That's not true. The only way that could happen is if you have a track multiple times in that playlist, or if you reload the playlist halfway through and you're using the standard random shuffle.

Removing any duplicates from your playlist, and using the 'least recently played first' shuffle will deal with both of these scenarios.
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Mk2a 60GB Blue. Serial 030102962 sig.mp3: File Format not Valid.