You should do it. You should also send along a couple more cheap games at Christmas, and maybe once or twice a year after that. I assume you're in the US, where 3DS games from several years ago may as well be free. I see a bunch at Gamestop for $1 to $5. Toss them in a Christmas card, and send over to him. If they get stolen by customs, who cares? Buy a couple more and try again.
A nice idea
duduspace11 "Well, since we are estimating costs, Pokemon Red/Blue did cost Nintendo about $50m to make back in 1996"
Mr Puggsly: "Hehe, I said good profit. You said big profit. Frankly, not losing money is what I meant by good. Don't get hung up on semantics"
Azzanation: "PS5 wouldn't sold out at launch without scalpers."