The cause of sports piracy and all of these weird deals is because games are most valuable in the regions of the participating teams. It's a Gordian Knot of rights issues, and it exists as a way to extract as much money from fans as possible.
And the teams want it this way -- both the Leafs and Canadiens are tied into telco/cableco ownership, who has a vested interest in getting you to pay more for games.
That's correct. If I lived in Montreal and wanted to watch all the Avalanche's games, there would be no issues. If I live in Montreal and want to watch the local team, I need to agree to get fucked three different ways.
And the teams want it this way -- both the Leafs and Canadiens are tied into telco/cableco ownership, who has a vested interest in getting you to pay more for games.