We were suppose to move to chip & pin in 2008. We didn't (what with our whole economy imploding around then nobody had any money to do crap like that). So there's tons of old hardware businesses were sold in 2005-2008 that never got used. The businesses are pissed that they spent hundreds (thousands?) on new terminals and readers that did nothing. So it's like pulling teeth to get them onboard. Imagine spending $800 on something that offered you little value but you have to, then you never use it and now you've got to spend another $400 (prices have dropped to be fair).
Oh, and we only do chip & signature, no pins, so the businesses are nervous they'll be made to buy even more hardware when chip & pin rolls out.
Now, I don't know about Canada but in Europe if your pin gets stolen you the consumer are liable (which is hilarious, because chip & pin has been broken before). In the US we have a law that keeps consumers blameless for any credit card transaction. That's because everytime you use your card you're borrowing money. Legally It's a loan (with 0% interest if paid off by the next billing cycle and if you pretend merchant fees don't exist). If somebody fraudulently borrows money in your name you're not on the hook in the US and it would take a major change in law that's not likely to happen (it would be tremendously unpopular and it would affect our upper middle class, and you don't screw with those guys).
Basically, one of the best parts of chip & pin (a major liability shift to the consumer) doesn't fly in the states. The businesses taking the cards get some liability shift but the Card companies themselves don't. So it's not as big a win for the various players here in the States as it was elsewhere. Add to that America's traditional aversion to infrastructure spending and you've got a product dead in the water.