#1 is less than two years away from legal adulthood. In his case that will mean guardianship, but more independence nonetheless.
So he gets more freedom, including an iPhone Facebook.app account I can monitor. He doesn't know the account password, I entered that into Facebook.app on his 2nd hand contract-free $10/month Paygo iPhone.
We review his Friend list and activity about 1-2 times a week, and of course I visit his page from my Facebook account and from his account. It's not foolproof of course -- like most 3rd party iPhone apps Facebook.app ignores the iOS Safari setting and allows unfettered web access via embedded Webkit. (Yes, Apple's parental controls are a joke. Android's are even worse.) At his age though, even that backdoor is a bit of a feature. It lets me more or less observe how he handles it.
So far, so good - but there's a twist. He likes to save images he finds on the pages of his High School friends and acquaintances. They are views into a world he cannot join; I grieve for that. I think, in his own way, he grieves as well. The pictures are generally benign, but they are pictures of 15-18 yo boys and girls. He is prone to share them via his iOS Photo Stream to his brother and I.
And that's the twist. Pictures that are reasonably appropriate for the phone of a 16yo boy are not a great idea for the phone of a 50+ yo man. It took a week or two for me to think of this and turn off his photo stream. I'll have to simply review his phone, which is easy to do each night.
Tricky business being a special needs parent in the net age.