Earlier quoted context omitted.
Kid bought an old crappy yacht. Years later he's caught in serial insurance fraud transactions for boats and planes. The dollar ripoff values go from $40k to $100k's rapidly within a few years, and a few years later he's in jail. Guy is in this line of 'work' because he is an adrenaline junkie. It brings certain side benefits-- dealing in obscure obsolete aircraft and parts gives him means of leisure and more than a…
Why didn't insurers keep track of his record of filing claims and charge increasingly high premiums after his super-early claims?
But just like any other business, there's always another company willing to take a chance at a high-but-not-too-high premium, especially if you're flashy enough with their agent. If the previous losses looked "plausible" or "unlikely to happen again" or the insured "has the financials of a good risk" or whatever, the policy will get written.