Here is some input . . . .
Continuos automated musical play list generator for windows / linux
( And its Free
Longplayer : http://lplayer.sourceforge.net
To time schedule the play of specific audio files -
like station Identification or promo's, try this. ( Free Also
Windows Scheduler : http://www.splinterware.com/products/wincron.htm
The only problem with this combination is, instead of the music fading out prior to the specific audio file being played, the music will abruptly stop playing and the specific audio file will start playing.
If there was a way to some how specify music fade out prior to the break in music - that would be a much added plus and more proffessional sounding.
One last thing - only a minor one though - the possible need for continous logging of files played. A script of some sort probably could be hashed out to log date / time / file name of a entire days / week / month broadcast. This should be easy by reading the xml output and time stamping it using the onboard time / date clock of the loging computer
Hope this helps. If you do think up a hack to fade out music prior to the break - by all means post the results here - would be most benificial to all.