In my game, the first song that should be playing when you first turn the stereo on, or in build/buy mode, never plays, but after that song ends, and the next song begins, I can always hear the music from then on. I've given up on trying to figure it out.
Hah. In one of my games, half the songs play, and half don't. It's literally every other song. If I leave build/buy on, it'll play the first song, but not the next. After the silence that the second song should occupy, it plays the third song. It goes on like that until it hits the first song. I thought my speakers were fucking up, until I realized that that happened to everyone.
The stereo songs mostly work... I think. To be honest, I'm almost glad. That first fucking Salsa song from TS2 haunts my dreams.