[Trident]

If you have paid for insurance and pay your $50 deductible after breaking your own phone, that's up to you. I won't say I've never done it.
The issue I have is with people who bully their way into getting a service that they don't deserve because they didn't pay for it. What makes it worse (for me) is that they act like they deserve it somehow. And if they encourage enough people to act as they do, eventually the option will disappear, as the financial model only works if people pay into the insurance plan.

I'm sure that I've paid way more than the cost of whatever phones I've replaced in all the time I've been with Sprint. But I'd rather pay the small insurance cost monthly than the high out-of-pocket full retail price when something happens.

You're right, there are two different sides with two different objectives- I'm sure Sprint/Asurion makes money on people like me. But that doesn't give people like the guy who flamed me the right to use the service contrary to the rules. If everyone did that, Asurion wouldn't be able to stay in business. And worse, we'd be paying a lot more for replacement phones.
His argument sounds like a defense of why it's OK to shoplift from stores.