I will be using this very process for two upcoming Christmas concerts performed by my church choir, the local junior college choir and community choir - one at the college's annual Vespers concert and a week later in our sanctuary.
 
I was able to purchase stem tracks of our work to supplement my rhythm section (piano, drums, bass, Ac & El guitar) and the few local brass & woodwind players we could round up.
 
I spent just yesterday setting up the Cakewalk projects.  I will have 13 tracks at the most and typically 9 tracks for each song going at a time.  At the college venue, our keyboard player will be running this from my SurfacePro 4 into a Behringer XR18 which has 8 assignable outputs with which we will feed the on stage sound system and IE monitors for the rhythm section and conductor.  At the church it will be located in the media booth and will use my MOTU 8M with an AD8000 via ADAT for 16 outputs total and send all tracks individually to our Allen & Heath Qu32 where the engineer can mix as needed.
 
I built my Playlist in Sonar Plat and gave it a trial run in my office.  Load times between songs was relatively fast - less than 10 seconds.  You have to set up each song in the playlist by right-clicking and choosing whether you want the next track to play automatically or wait for key press (Space Bar or Enter as a dialogue opens asking if you want to play the next track).  I also set up markers to correspond to the rehearsal markings in the score and then saved it with the Marker view open for efficient rehearsals.
 
We will do a dry run at our first combined rehearsal with both choir & orchestra on the 26th.  I too used the playlist with MIDI back in the day and loved it.  With today's technology, it should work just as well with audio.  I'll report back how it goes but I'm feeling very confident about it so far.
 
EDITed to correct misinformation.