I have a workaround for you; IL2 plays files in alphabetical order, this enables you to use a prefix(aaa, 001, etc) to determine the order files are played in.
If you use a high id(zzz, 999, etc) for the first file you play, you can later add files with a lower ID which will be played first.
IL2 refreshes the radio folder(I.E. starts from the first song) every time you tune to that station.
This should enable you to add new files while in flight, even if it doesn't allow for fully automated randomisation.
Keep in mind, using console(Shift-Tab) command "MUSIC PLAY STOP" skips to the next song in the alphabetical order, so you can't skip backwards or to new songs.
You can however play the first song in the directory using "MUSIC PLAY PATH [path to radio station directory]". This has the same effect as switching from and to the station.
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