Just to put in an idea: my 2 cents
I have seen this done by using macro example:
the Auto Intro and the same artist name - title of the song
In the playlist have a setting as a macro or trigger that when the macro is loaded it looks for a song Artist - Title of the same name
Example Playlist for the cloud version
(trackList) \music\ballad (random)
(trackList) \music\pop (random)
(trackList) \music\rock (random)
(trackList) \music\ballad (random)
(trackList) \music\pop (random)
(trackList) \music\rock (random)
(trackList) \music\ballad (random)
(trackList) \music\pop (random)
(trackList) \music\rock (random)
(trackList) \music\ballad (random)
(trackList) \music\pop\macro (random) when radio boss comes to this it loads song in playlist and then looks in the Intro\pop for same artist-title
Michael Jackson - Bad This being the intro
Michael Jackson - Bad This would be the song
(trackList) \music\rock (random)
(trackList) \music\ballad (random)
(trackList) \music\pop (random)
(trackList) \music\rock (random)
(trackList) \music\ballad (random)
(trackList) \music\pop (random)
(trackList) \music\rock (random)