jaime2000 comments on What makes buying insurance rational? - Less Wrong Discussion
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In addition to what everyone else said, I recommend Gwern's "Console Insurance". Also, Jacob from Early Retirement Extreme says the following about dental and vision insurance:
In the US, some kinds of insurance are really collective bargaining. Dental and vision usually aren't, but this is a reason to get health insurance even if you could afford to self insure.
If someone else is subsidizing the insurance, that can make it worthwhile.
In the U.S. You can often find the amount of the employer subsidy footer am insurance policy if you read the details of it. Also you pay for employer based health insurance (I think including dental and vision) with pre-tax dollars, which is in effect a government subsidy.