My house has four children in it. Three of them are two years old.
Of course you're talking about Apple being "the house", but in my case, the chance of accidental damage to the iPhone are probably higher than yours. No matter how much I plan to treat my expensive phone gently there are going to be times when it is vulnerable. If one child reaches for a hot stove, or falls into a pool, or picks up a screw driver with an eye on the electrical socket, or any number of immediate hazards, I won't take time to secure my expensive phone before rescuing the even more precious child. That leaves three children watching for the phone to become available.
The rule about the "always winning" with insurance is based on both time and a large number of people who purchase the insurance. Apple doesn't charge me more for AppleCare +, even though I live in a two story house with tile flooring and multiple high-energy children. I pay the same $199 as someone who is single, keeps the phone in an Otterbox, and always walks on the grass just in case.
From a financial point of view, it depends on your situation, which is something you know about better than I do (just as I know more about mine than you do).