I ran into the same problem and actually tried adding songs to the playlist using Winamp, and still couldn't get anything other than the default track. Eventually I realized that through modern computing i could tab out of Orbiter, play my music through iTunes as per usual, and tab back in.
Sometimes that can lead to orbiter not recognising keystrokes so I tend to run orbiter in windowed mode and have access to iTunes there. It's important to have quick and easy access to my ummu wakeup song collection.
True but I find it happens less in windowed mode than in full screen, I've also found that alt-tab can lead to some really interesting colour combinations on the MFD's so avoid it where possible
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