On one hand, I do think Count & WeHave are being pretty melodramatic here. I mean, c'mon now, we're all grown-ass adults here. We should all be able to handle our favourite sports team suffering a defeat against another team that we don't like, and the trash talk/good-natured ribbing that would follow it without crying about "tyranny" and "bullying", and then curling up in the fetal position and praying for death.
On the other hand, they're right that a Leafs/Habs matchup is a "no-lose" situation for the Leafs, and I see how that could be unappealing to some Hab fans. After all, the Habs are the team with the world's best goaltender in his prime, who traded PK Subban for Shea Weber because they have Stanley Cup aspirations in the here and now. And the Leafs are the team that finished in 30th place last year, and that virtually everybody in the hockey world thought had a better shot at another 1st overall pick this year than they did at a playoff spot. So, it's pretty obvious where all the pressure & expectations would lie.
Oh, and on the subject of "wear the local team's jersey to school or work days"...that doesn't really seem unreasonable to me, and it's something you should be prepared to live with if you don't support the "home team". Though banning other teams' jerseys is definitely a petty, BS move.