I was given a lot of freedom at a young age.
I started out with the big desktop in the computer room - My parents didn't monitor me all the time, but they checked on me.
Then they bought me a laptop, which stayed in my room since then. I'm on my third laptop right now, still in my room. Of course, I'm over 18 now.
As for gaming systems, Always had a playstation of xbox somewhere. Had the old ps1 in my room at first, and a ps2 in the living room (We all liked to play it)
After that, ps2 upstairs with me and the xbox 360 and kinect downstairs. It wasn't for the purpose of monitoring me, it was because me and Mom liked to play Dragon Age and Dad liked to play Ace Combat/Halo. So we all had access.
Honestly I was never monitored - But I was a pretty chill kid. I just liked the internet a lot. By age thirteen I had a guy in a chat room say he could find out where I lived. I knew enough about computers (And the information my computer could put out to others) to laugh in his face- I had everything set up to where no one could find out anything about me from my laptop.
I live in pick a state....
"I'm in middle school" This pin points the age to what? 12-14ish?
"I am a halfback on my soccer team for my School" easy enough to figure out what schools have soccer teams
Then you have things like my school colors are or my mascot is my team uniform is and bam... He's got you.
They do it slowly over time so one conversation may not do it but after a few weeks of stalking someone... you can usually get it......