HT204668: Locate and organize your iTunes media files
Learn about Locate and organize your iTunes media files
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Sep 1, 2015 3:18 PM in response to seanlivesindallasby Limnos,The labels will, as long as your friend's player supports tags (labels inside the files), most do. Depending upon how you move the files to the drive they will be ordered there simply as a large group of files by file name.
Artwork may or may not. If the files come from a source where artwork is embedded in the file it will. If it comes from a source where you have fetched the artwork using iTunes' fetch artwork feature it won't.
Make sure in copying the media you are being legal. Just because it is DRM free may not make it legal.