Obviously, the $250 + $215 premium is worth for it replacing 11K of gear. But $250 exceeds or is near the cost of most repairs and add-in the premium, you're really just paying for catastrophic coverage. If a 580 EX II were stolen, it would probably be better to just buy a new one than risk getting the policy canceled for too many claims when a used one is only a little more than the deductible. Even if I did make a claim, the deductible+premium is more than the cost of the 580 EX II. I think I will look around for a better deal at some point. I mostly just gravitied to the easy PPA coverage because of the bad experience with State Farm.
I am partially just whining a bit, I was in a hurry when I got the insurance and didn't include my Tamron 17-35, 50 f/1.4 and 5D on it mostly due to an oversight and because I wasn't sure how much longer I'd have the 5D. That's fine with me, although I should add them at some point, because I don't really need that stuff to stay in business if everything is stolen. Also, the stuff is insured closer to new value than what shrewd used purchasing would be, so I should be okay. Ironically, I didn't have insurance until the 50 f/1.4 rolled out of the bag and broke the AF. I'll get it fixed eventually and my annoyance that the deductible is high enough not having the insurance wouldn't have even mattered is balanced out by solace in knowing the $200 I saved in not having insurance for a year is more than what it'll cost (probably) to get the 50 f/1.4 fixed.