The holy grail of Apple DRM for me is opening up the audiobooks. These files cost a fortune, can't be easily burned and re-ripped (and some even come flagged as "non-burnable" -- showing that there are crippleware modes in iTunes that aren't widely known). Cracking them through the analog hole using Audio Hijack is time-consuming (I spent six weeks this year running two PowerBooks 24/7 to convert all my iTunes audiobooks to MP3s using this method).
I write books. My latest is a YA science fiction novel called Homeland (it's the sequel to Little Brother). More books: Rapture of the Nerds (a novel, with Charlie Stross); With a Little Help (short stories); and The Great Big Beautiful Tomorrow (novella and nonfic). I speak all over the place and I tweet and tumble, too.