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I remember this one guitarist I worked with, who rode a motorcycle and didn't own a home, but rented a fabulous rent-control apartment in Santa Monica. He self-insured. He paid a bare liability on his motorcycle, but banked every cent he would have otherwise paid for health, vehicle, homeowner's, fire, flood, earthquake, renter's and all the other insurance that we pay $24,000-to-$26,000 per year for. He didn't trust an insurance policy to pay $hit if he filed a claim. He had stories ... man, did he have stories. He used to brag about how he would be a millionaire just on the money he saved from paying premiums that would just disappear. He even showed me a box that he was filling with Krugerrands that he was buying with all the would-be insurance premiums. That was in the early-80s.
Now, he has a townhouse in Newport Beach and a townhouse on a golf course in Scottsdale, two of the most beautiful Harleys imaginable, season tickets to the Angels and Lakers, and several other compelling symbols of disposable wealth. And he's the picture of health. The reason that he only owns townhouses, rather than mansions, is that he pays for all that stuff in cash. He's 51 and has been retired for about seven years and has virtually no monthly payments. (I suppose he insures his condos, but you never know.)
I dutifully pay my thousands in premiums each year like I am almost required to do. But, after doing so for over 30 years, I am still waiting to see an insurance company actually handle one of my few claims responsibly.
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