I play live with BIAB regularly, in fact 5 times next week. My process is this-
I bring a MacBook to the job.
I use the jukebox to load and play my set lists.
To start with all of my arranged song files are in one folder.
I make a copy of that folder so that I am not working with the original files on the performance.
In the copied folder I assign a number to the songs that are to be used and the jukebox will play them in order. 01, 02, 03 etc.
I prefer to have the jukebox set up so that the space bar starts each song.
Matt has a valid point and I do have a usb output device however in over 4 years of using the earphone jack I have never had a problem.
I use program on the MacBook called Boom which is an EQ for all the output of the computer. Depending on the size of the venue, my sound systems include a full PA and 2 other powered speakers, 12" and 8". The Boom allows me to save a preset EQ for each of the sound systems.
I hope this helps.