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I cannot speak for the Canadian side of the issue because I am not based in Canada. I can only speak for the US side. And US-wise, it is legal. It is completely lawful to transfer money from a non-profit (or a for-profit) to someone in USA, for a trust or otherwise. There is simply no oversight as to who the money is transferred to. It may be transferred to anyone.
Civilly, one may wish to ensure that the non-profit and the trust are both doing whatever is in their bylaws/instruments as necessary, of course.
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