Running High Sierra 10.13.6. Recordbox 5.4.0. Sandisk extreme 256gb. When I sync the playlists only the artwork and titles move onto the USB. The content folder is missing on the USB drive.
I've tried other drives and found that it's only an issue with this drive I just bought. I've reformatted several times and made my best efforts to get this unit working but I cannot seem to be able to get it to take. 
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on HFS formatted drives the contents folder is hidden.
Try if the tracks load from the device part of the Rekordbox tree and most likely all will be there.
for maximum compatibility format FAT32 (mbr)
Thank you for your helpful response! Sadly it didn't work still.
Disk Utility shows only very little data after syncing hundreds of songs. Only the art and track info is making it over to the USB it seems. That is showing up on my XDJ1000 mk2 when inserted and scrolled through.