Is there any way for you to let the playlist decide randomly which piece to play, but only once in each “loop”? Like when it selects the first song, it won’t select it again until it has played every track in that list? So I when I hear the track again it will be from the next “cycle”? So I don’t hear the same track played five times in a row, but I do want the playing to go on for ever and not just playing the list once.
WinAmp has a control in Preferences -> Playlist called ‘Shuffle Morph Rate’ that allows you to change how radically the playlist shuffles each time through. Is this what you want?