Hook the PB up to your computer with the USB cable that came with it, then use Desktop Manager to sync the music/playlists/etc. you want to the PB. Very simple.
Looking for a simple yes or no that iTunes will work in the PB. If so, how do you do it and what's needed.
Not sure I understand but the Playbook plays NEWER iTunes MUSIC files pretty well without any issues. Only older, DRM protected files, don't play.
Of course you can't transfer any iTunes music videos, TV shows or movies to your playbook since all these are DRM protected and do not play on the Playbook.
Just copy the music files from your iTune music library directly to your Playbook and you'll be fine.