I guess if you're the sort of person who buys $1 nonsense on eBay this could even sort-of work.
But if you bought something actually valuable, the insurance is useless _even if it paid out_ which it never has. This is because the huge headline dollar value is the _total_ sum insured and individual claims are strictly limited to a far smaller amount.
Let's try an analogy. Imagine if Coca-Cola took out $10M insurance against Coke causing brain damage. Then it turns out Coke has caused serious and irreversible brain damage to everyone in the world who drank it in the last 50 years. Oops. The insurer says OK, just individually post us proof your brain damage was caused by Coke and you'll get 5¢ each. It won't cover the cost of postage, but too bad, up to 200 million people can claim on this insurance, and at $10M total that's five cents each so that's the maximum claim.
That's how the SSL "Insurance" works. People who can prove they reasonably relied on the insured certificate AND can prove they were damaged financially as a result can claim up to a fixed tiny sum of money, which isn't worth doing.
The insurance firms selling it know this is worthless, it would be illegal to sell such pointless insurance products to consumers in most of Europe, but fortunately they sell it to the Certificate Authority which isn't a consumer, and the CA has no reason to care that it's useless, it sounds impressive.