Agree that dealing with Canada CAN be a headache. Even mail takes a long time to get there. IMO: The Canadian government has deliberately and consciously set out to make individual transactions between our two countries difficult. When larger items or UPS or FedEx are involved things can go south in a hurry. The buyer may receive a bill for taxes or duties weeks after the item has arrived.
I had a Classe amp once, when sent in for service it was sent to NY and driven across the border. Classe drove it back to NY from whence it was returned to me. Even they had to find a way around the bureaucracy although somewhat inefficient.
Having said that, I deal frequently with Canadian companies such as PartsConneXion and have sent small items to Canada by USPS with no problems. So some transactions can hassle free.