What does the richest do in this situation? Surely some must feel the need for their kids to venture out on their own, or do they live in a neighborhood where these types of policing doesn't happen?
A large, wealthy estate is sort of like a neighborhood. Brad Pitt built a skate park in his backyard for his children.
Yeah, it’s not even a question regarding the richest, but change it to upper middle class families with busy and reasonably wealthy parents living somewhere in dense urban NYC downtown and it’s interesting how they go about it.
Gated neighbourhoods and at some level suburbs that are simply unwalkable for everyone.
This is how I grew up (well, not wealthy, but a dense, residential neighborhood in Manhattan): it was perfectly normal for me to walk around and take the subway alone by the time I was 8 or so. I don’t remember ever being stopped by anyone, police or otherwise. This was in the early-mid 2000s, and my perception is that it hasn’t changed much in the city.