Rule 10b5-1 plans and Form 144 drips presuppose a liquid public stock and a US insider-trading regime. Neither applies to a private Ontario corporation.
Delaware trusts and 501(c) foundation sleeves presuppose US domicile and a US charitable-deduction regime. The Canadian charitable structures are different enough that the analogy misleads more than it helps.
The generation-skipping transfer tax, which is the whole reason Goldfarb’s gifts go to grandchildren’s trusts rather than his son’s, does not exist in Canada at all.