I...bought...twenty shares of Augury Insurance (which sells auto insurance — a good bet, considering all the cars I've been wrecking) I'd argue the opposite, no? The 100-year-storm of destruction that we, as Player 1, unleash upon the poor Liberty City automotive world would probably make any insurance company run screaming and crying in the opposite direction of profitability. "We had HOW MANY claims yesterday after…
Did I say casinos? I meant insurance companies.
Seriously, insurance is a bet on something bad happening. Usually it only makes sense to buy insurance for the equivalent of long-shot "lottery jackpots". Like a catastrophic health problem. Or like the damage you might do to other people and their property in an auto accident --- but probably _not_ the damage to your own car. i.e. Insure for personal liability calamities, but not collision damage if you could pay for it out of savings.