idk what crossfade means (yea, totally stupid), but I know doubletwist is made for ppl coming from itunes. itll take ur tunes music & playlists and let u sync ur druid via usb for free or wirelessly for$ 5.99. there's even a youtube video telling u like step by step how to do it... ill find the link for that. but just know that if ur music is drm protected, doubletwist wont like fix that for u.