It's an interesting post, but I always wonder about people who say companies should be smarter than they are, especially when it comes to risk management. Preventing expensive bad things from happening requires somebody's attention, and often, it is a lot more remunerative to instead pay attention to things that _make_ money than things that avoid _losing_ money. You can take this conservative (hanging on to what you have) approach too far.
So I went looking back through the blog a few days to try to get a sense of the blogger. Is this a person who thinks about costs in a nuanced way, in a way that captures several stages of consequences of multiple approaches when making a decision?
Short answer: No. This blogger is a genuinely decent human being who thinks carefully and tries hard, but is still making rookie errors. When I tried to explain it to R., he kept saying, yeah, you shouldn't insure jewelry because you'll wind up paying for it in 20 years (which is how the policies are priced). Except my point is that if you own something expensive enough and likely enough to be lost or stolen that you're tempted to buy insurance, then you're going to be paying for it in a lot less time -- more like five years -- _when_ you do lose it, in the form of increased premium costs. On _everything_. In the comments thread, the blogger is surprised at how little it takes to get dropped from an umbrella policy.
Commenters stepped in with a variety of explanations for why insuring jewelry with your homeowners is a mistake and the conversation wanders, but the blogger is still hoping for detailed rules from the insurer so he knows whether he should file a claim or not.
Which is ridiculous. There's a rule. It's simple: you never make a claim if you can possibly avoid it. Once you _do_ make a claim, you expect to be reimbursing the company for having made that claim. Forever. Which is why you never make a claim if you can possibly avoid it.
There's another theory about how insurance works (and it involves Getting Your Money's Worth Out of Premium Payments). That theory is inflationary.