I'm on a MAC. The first time I exported to USB, there were two folders, one labeled "Content" (with artist folders inside) and one labeled "Pioneer". Later, my DJ friends told me to organize songs in sub playlists by genera. So I did. Then I erased my USB and tried to export my new playlists to it. Nothing happened, the stick was empty. I reformatted the stick and this time it worked, but there was no folder labeled "Pioneer." When I got to the club, the DJ controller couldn't read the stick. When I got home I reformatted the stick yet again, and this time selected "master Root", but there's still only the "Contents" folder and no "Pioneer" folder. Is this ok? Does it need the Pioneer folder? The lack of information or any feedback from the software when things aren't working is really frustrating. Otherwise, if I can get it to work, it looks like amazing software.
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Now, under Preferences-Analysis in Rekordbox, I find a listing for "Pioneer folder" and in it's window is a file path: /Users/jerrybennett/library/Pioneer/rekordbox. I've searched on my computer, no such file path exists.
For MAC users. Format USB drive to FAT. If you can change the scheme, use Master Root. This worked for me. Also, I couldn't find my Library folder because, for some stupid reason, Apple now hides it.