Sounds like the startup environment (I'm talking 1-8 employees) would be a better fit. I too interned at a big company. Don't let it ruin the industry altogether!
So moral absolutes apply to adults but not children? There is never a case when spying on an adult could save their life?
I'm not sure about your examples. If you suspect your child may be suicidal, talk to him or her. If you do NOT suspect bullying or cutting, how do you know that spying is justified? I think you're "begging the question."
An up-to-date iPhone is not trivial to jailbreak, especially if it isn't yours. Jailbreaking is a specific kind of rooting. It "ought" to be virtually impossible.
Then good luck hiding your trail, reassociating the Apple ID, hoping no apps broke due to the jailbreak (it's happened to me), keeping the device associated with the owner's iTunes, etc.
Apple gets the press, but there is no Flash on 98% of cellphones in the wild. Or IE8 64-bit. Or Linux in 64-bit. What about people who only own a cell phone (VERY common in other countries)? What is Adobe offering them? Stop assuming everyone is a rich technophile.