I wrote a powershell script that'll copy an itunes library to a flash drive converting any Apple Lossless files to FLAC in the process. It will also create a folder called Playlists and copy songs there too. Get it from: joshmackey/TeslaMusicCopy · GitHub Get FFMPEG (for converting) here: Zeranoe FFmpeg - Builds Make sure to grab the latest static version. EDIT: Sorry Mac users, but this is windows only. Mac version can be found here: Easy iTunes playlist syncing for Tesla USB flash drive