Ok so the I fixed the leveling issue, and used the jukebox and everything was going swimmingly until rehearsal last night. When one song finishes and I hit stop on the JB, and kick it to the next song, the next song will start playing toward the end of the file instead of at the beginning. So I have to fiddle with it to get to the begining of the next file.

Note I have deselected random, and selected "stop between songs" I thought it was because some of my files had extra measures at the end, but then I noticed that it would "play" grey measures in the file after the file was over in many of the songs.