just don't worry about it. Put all your cigars in your checked luggage, not in your carry on. Only claim what you are supposed to claim, 150 cigars. Then anything over that amount keep on you in your jacket, split up between the three of you. Or just pay the duty, it's not too much I don't think.

I think I am leaving on the same flight as you. I leave Calgary at 9:40 for the DR. What about you?