I can see how you associate it being the least secure with it being the most awesome. I don't see what could go wrong with your ability to take some legitimate and important criticism about something you like and turn it into something awesome about said thing.

Mac's always go down quickly in these contests. The people who make it happen often say that its considerably easier.

edit: Charlie Miller: "It's really simple. Safari on the Mac is easier to exploit. The things that Windows do to make it harder (for an exploit to work), Macs don't do. Hacking into Macs is so much easier." - http://www.zdnet.com/blog/security/questions-for-pwn2own-hac...