Would it be an option to get him on a motocross machine first? If you fear that heīs probably going to fall off a motorcycle, it wouldnīt hurt as much in a cross machine, but could have the same impact on him (like "oh hey, it hurts when I do this and that").
Or better, tell him if he buys a bike, he has to attend a safety course and maybe a guided track day later. The better his skills, the lower the chances of him falling off.
In regards to the mechanical side, your idea of "letīs do this together" is really good. He is going to have to make some experience the hard way. I had to at least, learning that being aware of what youīre doing will have an effect on your safety. Like that one day at the race track, when I came back to the pits and was staring at my rear wheel. It looked somewhat strange... with the big sprocket nut missing... urgh....
In the end, you canīt help your son if heīs acting crazy in traffic. I think we all have been there and acted like idiots. Maybe thatīs part of the experience.
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