I enjoyed the one on cheap recreation. I think he might be overstating how common helicopter moms are...I'm a millenial (barf) and my friends and I spent tons of time doing unstructured activities! Many of them revolved around getting drunk and smoking pot haha.
I'm sure some areas of the country lend themselves better to unstructured activities than others though. As a Vermont kid it was always pretty easy to go hiking or go down to the river and waste away an evening next to a campfire. I don't think that would be true if I grew up in some hellish suburb or next to a strip mall.