I feel the article as well as most of the comments miss the most important difference between the two. Insurance, assuming the fee isn't too high, increases your utility of money while gambling decrease it. If there is an event that happens 1 time in 100 that costs you $100k and you pay $1.05k to insure against that would have a negative expected value in money terms but positive expected value in utility of money te…
Critically, the variable that makes gambling rational is the hedonistic pleasure one derives from it.
Insurance versus gambling seems like a penetrating question, but as you describe, it really is not. The more-germane one is gambling versus drinking or theme parks or mindless television.