Something that the OP only briefly touched on that I feel has really fallen by the wayside is RESPECT. If you let your kid wander around the neighborhood unsupervised, fine, but they better be respectful enough not to mess around with my stuff. I don't care about seeing groups of kids wandering around with frisbees and soccer balls but I get pretty worked up when I see them with spray paint or knocking over trash cans, etc. However you do it, the kid needs to learn respect before (s)he get's the freedom. OP touched on this a little with the "Don't automatically take your kid's side" portion but I really felt that needed to be expanded upon. Respectful kids don't need (nearly as much) supervision.
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These are the good old days.
How did I become upright?
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