I voted Silas up as well because it's an important point but it shouldn't be taken as a general reason to buy as much insurance as possible (I doubt Silas intended it that way either). Jonathan_Graehl's point that you should self-insure if you can afford to and only take insurance for risks you cannot afford to self-insure is probably the right balance.
Personally I don't directly pay for any insurance. I live in Canada (universal health coverage) and have extended health insurance through work (much to my dismay I cannot decline it in favor of cash) which means I have far more health insurance than I would purchase with my own money. Given my aversion to paperwork I don't even fully use what I have. I do not own a house or a car which are the other two areas arguably worth insuring. I don't have dependents so have no need for life or disability coverage. All other forms of insurance fall into the 'self-insure' category for me given my relatively low risk aversion.
To whom it may concern:
This thread is for the discussion of Less Wrong topics that have not appeared in recent posts. If a discussion gets unwieldy, celebrate by turning it into a top-level post.
(After the critical success of part II, and the strong box office sales of part III in spite of mixed reviews, will part IV finally see the June Open Thread jump the shark?)