Another new idea: Radio DJ (or what it should called?)
Every X number of songs played and reach JUKE_SONG_FINISH, set the jukebox software player to pause, the play some ad, radio noise, speak or whatever. When that played finished by the plugin, let it resume the song again. Some software might have changed the song and send a JUKE_SONG_START, but a plugin can just send PAUSE request again while this accour.
To make sure the user cant RESUME, simple send a PAUSE request again after that, until the ad is played finish.
These can been done using PAUSE/RESUME events throuch a defined event (Which might called diffecent in various software).