The by-law is also vague with potential over-reach. Is a 12 year old walking home from school and up the driveway going to need to arrange supervision for the last bit of their journey lest they be in breach of the by-law?
It seems to me that each OC should work out whether they need such a rule for specific areas presenting real risk and if there is a risk, whether that risk could be minimised some other way than through a by-law.
The by-law is about “playing”, which is different from someone walking to/from their residence.