So, the parameters of the strategy are set by the goal of taking back hockey. The Canadians only need to occupy key routes through the US to misplaced hockey teams--those in Arizona, Florida (2 teams!?), Tennessee, North Carolina, and California. Note that the strategy would leave a few teams in the hot zone: The Mighty Ducks of Anaheim so as not to offend the awesome power that is Disney (Canadians like Star Wars and Toy Story too much to alienate these folks); the Dallas Stars (to keep alive the mythic affinity between Texas and Alberta). The difficulty here is that all of these targets, except NHL headquarters in NYC, require traveling over long stretches of hostile terrain. So, one of the keys to this is:
Timing: Winter! Of course, not just because this is when Canadian passions will be at their height but because the Americans handle winter so poorly. Indeed, a potential tactic might be to water the cold roads of the northern US to create icy roads that will limit the ability of the Americans to fight back on the key roads. The Canadians could then patrol I-5 and I-95 and similar highways on skates.
But how will the Canadians defeat the US military? First, by encouraging the US to continue to stress its forces in distant Mideast wars. Notice Stephen Harper's more hostile than thou approach to Iran. Second, the deployment of increasing numbers of Tim Horton's franchises should help to slow the American response by, well, encouraging American obesity. Third, Canada co-commands NORAD--the North American Aerospace Defense Command. They could use the positions here to confuse the Americans--to insist that the first wave (and only wave, given the numbers of CF helos and planes) of attacks are merely Canadian geese migrating south. If the attack is timed with the Super Bowl (akin to Israel's Yom Kippur?), then the Americans will be taken by surprise.
The big question is: could they hold the highways for a week or so while the trucks run down, grab the Panthers, the Hurricanes, the Coyotes, and the other misplaced teams, before enough resistance builds?* Well, the US is late to most wars it fights, so it might just work.
* The Canadian special ops units would be focused on Gary Bettman and the NHL HQ in NYC.
As long as the Canadians do not insist on changing American signs to add extra "u"'s and changing lots of "s"'s to "c"s (as in defence), the Americans may not even notice. The Canadian troops would be trained to speak in more declarative sentences and cut the "eh's" so that the Americans would just assume that the uniformed folks are just American troops with less equipment.