A:
Yes, DRM-free iTunes songs, podcast videos, or even playlists can be transferred and played back on your Walkman®.
Songs purchased from the iTunes online music store that contain DRM copy protection will not play back.
You can do this using "Content Transfer" a program supplied on the software CD included with the Walkman®. the program will access the music library within iTunes allowing you to easily transfer your DRM free songs to the Walkman.
iTunes will not directly transfer to any non apple product. please contact Apple to request other MP3 players connectivity within their program.