You don't raise a rebel by telling them it's okay to play on the roof.

You raise a rebel by telling them "I don't want to see you on that motherfucking roof!"

Then, when they are ready, they will go to the roof.

You provide the back pressure and their job is to overcome it.

How much back pressure? That's an exercise left to the parent.

For my money, I want the few rebels who survive helicopter parents.

These kids may be milquetoast with no sense of evaluating risk.