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I seem to hear this attitude a lot here. That's ok I guess, personal preference and all.
But try applying that argument down at your state DMV (MVD). "Honest, I don't need car insurance. I've never been in an accident and I'm pretty careful. Nothing will happen! No really, I'm willing to gamble that I won't hit anyone and that no one will hit me!"
Yes, I know, there's really no comparison because the state requires you to have car insurance and we're talking about phones, not cars. But my point is that as careful as you may be – there's always someone/something else out there. Consider it as a warranty/insurance protecting you not from yourself, but from others and/or your environment.
With car insurance the problem is that you can cause enormous damage with a car, much more than you could ever pay for yourself, so you are forced to pay for third party insurance to make sure innocent victims will get compensated. Even if you were not forced, driving a car you can quite easily create damage that would bankrupt you.
With things like an iPhone, the question is: Can you afford to pay for the damage? If the answer is yes, don't pay insurance. The insurance will make profit (and will have overheads), so on average you are better off taking the risk.
The reason you are required to have insurance on a car isn't because of your property. It's because of the potential damage you do to another persons property (or life for that matter). $20,000 damage in an accident isn't exactly disposable income for nearly anyone. You total another person's car, they shouldn't have to foot the bill.
$20,000 is cheap. You are thinking about the car; think about injuries. You hit a 20 year old who will live in a wheelchair for the next 50 years. That's real money. Having to pay $20,000 hurts, but injuries could cost millions.
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