I'd come across kids and parents like this when I worked at an indoor park. I saw parents yelling at kids because they were afraid to go down with a trick. The parents were always looking for free shit (even though none of them were poor). They'd even drive out ASR/Agenda to try to sell their children. The parents were super annoying.
However, the absolute kookiest situation I ever saw was Jett and Jagger's Kids That Rip indoor park. The family owned gymnastics facility, added a skatepark, took the kids out of school, hired local dudes to work the park/teach the kids, and forced the kids to do a list of tricks each day before they could go home. Everyday was skateboard practice.