While I was delivering papers at 11, the infrastructure for that is no longer available. My suggestion is that he help neighbors with yard work for minimum wage. $4 per hour goes to the neighbor he owes and he keeps the rest. Debt is paid after 25 hours of labor. of course, the likelihood of that sort of kid actually doing and real work is very slim.
"What If" is pretty neat, but only in small doses. I tried to read all of them and got lost. Not on the physics or math. On the whiplash assumptions he needs to make the questions answerable.
As someone who gets paid to sit on hold for clients, I have developed a few techniques. The first is to get a portable phone with a headset. The second is to save laundry folding until I am on hold. The third is to find a website with neat articles that can be read in 60 to 90 seconds.