If you want to have some "illiterate" to do this for the artist's show, I strongly recommend to provide a hardware device to trigger the songs (Buttons, Pads or Foot pedals, a cheap Midi keyboard might do as well).
I am not experienced with "looping" and "song firing" applications, but there have been a lot of threads in these forums about such things (this is where I learned about "region playlist", which I do believe can do loops including loop count ->
https://forum.cockos.com/showthread.php?t=208818#4 ). You might also consider "Playtime" ->
https://forum.cockos.com/showthread.php?t=149712 , and "Driven by Moss" ->
https://forum.cockos.com/showthread.php?t=206610 .
-Michael