The only way to make them restart is to have actions that reload the files into memory again, it seems. It doesn't hiccup the game as it probably remembers the tracks still (or however it works), but I didn't want to do that because of the chance there ARE hiccups (I'm pretty pedantic about it), and it requires an event for each song that can play in a layout. Not a big sacrifice, but a "workaround" nonetheless!
And I'd love to have the file, as I've been planning to enter IGF by Nov 1. That would be awesome!
EDIT: Is it somehow inherent to DirectX to set if a sample loops when you load it, rather than when you play it?