Re: Either he was a total n00b or there are known weaknesses in the iCloud
0 day exploits happen...and surprise companies...otherwise they wouldn't 0dayers.
I have some sympathy with your second comment, sloppy systems are not just a fault of the criminal.
Insurances companies don't pay out for buglaries when you leave the house unlocked for a reason. They also increase your premiums when you claim for items you lose/damage.