I think it will be problematic for all the reasons you mentioned. Scott is probably better prepared to answer that, but it might make sense for someone to run a Can-RR and make sure it hits people in the different regions (Maritimes to the west coast).

Maybe there would be someone in Winsor/Detroit or Niagra who could "run it over the border" and mail it from the other side and this could be scheduled in to the list (first half in the US, second half in Canada).

As a side note, I visit a lot of Canadian casinos and make sure to bring home a few sets for the people in Jersey. Whenever I pass through any of the security checkpoints they have to go through my luggage and look at the chips. It seems that the xray/xray tech cannot figure out what it is (it does look like a stick of TNT when stacked).