I was looking at this phone for kids recently: http://tinitell.com/ - just GPS and voice, but let's a kid be in contact.

I'd be curious if people have tried this sort of thing, and if it works... mostly if it works psychologically. Do you find yourself really giving your kid more freedom? Does it address the anxieties that keep us from giving kids freedom?

It doesn't address the highly structured time, but at least I'm doing OK there by just not opting in to most structured activities.