Just thought I quickly share my experience with getting the files on your LP-16 with a Mac.
Although I have installed the latest firmware update (83859) the LP-16 is still having issues with some hidden files OSX creates.. namely the .DS_Store files. At least on my LP-16 with Release Build 83859 it’s still not happy displaying folder which contain those files as MT songs.
What worked for me is to show the hidden files in OSX and then just deleting them manually from the USB drive. Here are helpful instructions to create a little Automator script to toggle your hidden files on OSX. https://blog.bertvanlangen.com/articles/toggle-hidden-files-finder-os-x-10-10-yosemite/
Since I did that all songs are working and the unit is running stable. Ready for Rock&Roll! (or even 80s pop…)