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@lae
I also hate it. There's a little bit of an age gap between my little brother and I - well, fifteen years - and the dynamic is similar to you and your son; he just goes flying off (at a good 12-15mph) swapping between the road and the pavement completely arbitrarily and without shoulder-checking. He's slowly getting better but still picks up terrible habits from my parents (like cycling in the door zone).
The funny thing is that he's a complete wimp off-road. Walks over every dropoff and holds his brakes down any incline. Natural roadie, perhaps.
Every time I go and visit I try to tell my parents that they all need cycle training, but they're apathetic (about everything).