I don't think it's unreasonable to have a child pair up with a sibling when going around the neighborhood. I don't see anywhere in the question where the parent describes the neighborhood they are living in, so it is reasonable to question what kind of environment it is that the child is walking out into. It's great that a neighbor paid the child to deliver flyers, but there isn't much explanation of the neighbor either. I would assume that the parent has a better handle of what the almost 12-year-old is allowed to do. In a good neighborhood with a responsible child, sure... 12 is certainly old enough. It's also acceptable to have him take his SISTER along with him (without insulting his masculinity and damaging his budding ego). I don't think an apology is necessary, at least on the parent's part. If he is not old enough to realize that throwing a helmet through glass is a bad idea, I'm guessing he shouldn't roam the neighborhood by himself.