I get the sense that the jack of all trades has a more enjoyable life, but often is left with more difficulties too - so it kind of balances in some way.

I really can not imagine any parent letting their kid ride a bike fifteen miles to go fishing at the lake, alone.

In Finland perhaps. Here, people are still pretty trusting, letting their young kids walk to school and the like - though I get your point. I remember when I was about 8, I rode with a friend about that distance to drop a "love letter" in the letterbox of a girl I liked :)