Yes, and you can even use <Random> to get the files in a random order in the folder: https://www.mediamonkey.com/wiki/index.php?title=WebHelp:Configuring_Directory_and_File_Formats/4.0

So, for example a Sync Mask of <Playlist>\<Random> <Artist> - <Title> would get you files synced by Playlist folder in a random order.

Sync: https://www.mediamonkey.com/wiki/index.php?title=WebHelp:USB_Mass_Storage_Devices/4.0

is there a way to save my library to a thumb drive without the entire file structure, just the files. I have a device that is not shuffling my synchronized version, and I think it might be the folders that is confusing it.