Mark,I love those one man brake bleeders you can buy they make the job so much easier. I think I've used up all of my brake bleed assistants
the booster is just a booster and is not needed to bleed fluid. It just provides additional pressure to help apply brakes. The system with a bleeder cracked is light.
I've been watching your progress with your sons first car and I thinks it's great that you are sharing the same passion.
I'd be trying to put a minimum of a kit in each cylinder and master before letting him on the road. (light hone first). Without trying to "stick my nose in where it not wanted" It's possibly one place where I'd "help" him.
It's a great story you dont often see father and son working on the same love.
Cheers
Warren