I use Bass so I don't have any generic code to share, but I wanted to say I'm using 6 short loops of music for a small project I'm working on, and then in the main loop I just check to see if the current track is done playing, if it is, I select a random loop to play. Once in a while you get a ever so slight delay before the next track plays due to main loop hiccups, etc, but it's not really noticeable in game.
So anyway, instead of a static looping piece, now it seems like it's a never ending stream of music. Works well. :) When you do this, ofcourse the music loops need to sound similar and blend well. ;)
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