I think it's prudent to wear helmets when tobogganing.
While you control your speed I think the most dangerous parts is other people crashing into you and you smashing into the ground. So to me the risk is no different than biking, skating, and skiing. All activities where my kids where helmets. I know growing up I smashed my head pretty good tobaggining without being too stupid about it.
I find it interesting that you concerned with him relying too much on safety equipment. I think that concern in general is overblown when comparing to the consequence of head injury. And while I agree you want your kids to learn by non permenantlymhurting themselves before they permenantly hurt themselves the head is not the place for that. Elbows and knees can be scraped up to get that feed back
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