Dapper makes transferring your playlists,
music and album art from iTunes or a folder on your Mac to your Digital Audio Player easy! You can customize it to your
player or choose from built-in DAP definitions. (Eg FiiO, iBasso, HiFiMan, Sony, Onkyo etc) See http://www.map-pin.com/dapper/ for DAP list and more information.
Use a simple slider to select which artists music will be copied to which storage device and see in real-time what amount of storage will be used as a result.
Dapper supports a host of options e.g.:
Multithreaded to copy to two drives simultaneously.
Auto sync on DAP connection.
Clean up OS X files on DAP storage.
Reformat capitalization of filenames.
Artwork extraction to folder.jpg
Sync additional external folder for DSD or FLAC files
Warn when more than nn MB of data will be changed.
Need to convert your FLAC files into iTunes Apple Lossless Audio Codec (ALAC)? - Download FlacTunes here on the App Store.
Finally, Dapper is licensed by the number of songs you have in the playlists you set up Dapper to sync to your DAP if you do not choose the full in-app unlock.