This is the core problem. It doesn't matter if you convince Mom & Dad & the kids to play risky if the primary "risk" is getting picked up by the police and having your family fed into the bureaucratic grinder of Child Protective Services. Society isn't just encouraging the removal of risky play, it is enforcing it. Until the police are trained to get a call to a child riding their bike down the road by themselves and berate the person who called them and not issue even a token warning to the kid or parents, there will be no change.
Not to deny that this is an increasingly litigious society, but if the bureaucracy is so sprawling, surely it gets to a level where it's too stuffed with requests to be able to respond to every triviality, no?
Feeding people into the bureaucracy machine is quick, easy and looks good on your KPIs, so that is where the focus is. Helping people get out of the bureaucracy is hard and time consuming, so that mostly gets ignored. Being stuck in limbo for years with a pending CPS case would be shattering to most people, even if nothing concrete ends up happening.
It doesn't work that way, because bureaucracies do not have to operate on a first-come, first-serve basis. Across the time span of years, anyone can find themselves part of a politically-targeted group and find their case jumps the queue. I prefer to avoid that anti-lottery ticket if I can.
Things are made “safe” because there is now always a risk of getting sued when stuff happens.