I simply look at it as what it will really cost for me to live in paradise with peace of mind. Knowing that one day we will have to potentially lock it up and walk away and possibly never see it again.
Thanks to the self insured around here, you can get some smokin deals on homes since the storm. Either from those who do not want to endure it again, or those who can not afford to chance another blow.
Some people can self insure and go through life without a scratch, others will go bankrupt. It is all a gamble same as going into a casino and putting it on a table (just different odds).
Having done the math, I do see your point about many not being able to insure themselves. I personally would never dream of moving to the island without insurance. That is just me, others opinions will obviously vary,it just depends on your experiences in life, how big your savings account is and if you feel comfortable laying it all on the line.
My one caveat to this argument would be, if I were renting and could just wave goodbye to whatever personal items I left behind and stood to lose less than say 10K.