We've raised two boys: One is 21 and a recently discharged Army combat engineer; one just turned 19. Both have ridden pillion with us since their early teens, were put through basic classes, and at least partly relied on a motorcycle for basic transportation since then. Neither has any meaningful off-road experience. Each has ridden to Laguna Seca, a 2000 mile round trip including lane splitting through Bay Area traffic, before they were 18. I think I can meet your 'BTDT' qualification.
IMO, your attitude and actions will have a lot to do with how they ride (and drive). So, go set the example you want them to live by (possibly literally).
(Note in my case, both of us teach motorcycle safety, so the boys were raised with TWO motorcycle safety nazis to answer to...)