Firstly, Montreal isn't exactly a bastion of Canada love. It's hard to say more without the paranoid thread monitors coming in and screaming at me for daring to speak about it. Just notice the particular things they were complaining about. Second, Toronto is its own beast in many respects. The city pretty well can and does exist "outside" of greater Canada. Hard to describe what I mean but there's definitely a sense of independence in Toronto that I don't see anywhere else in the country. It's kind of ironic that 2 of our oldest cities, with so much history that define this country, sometimes feel a bit distant. Or maybe that's just my western perspective. But I've definitely picked up the vibe you describe when visiting there.
I see plenty of people wearing Canadian-themed clothing and it would never occur to me to make tourist jokes. Maybe it's just more common here, or maybe you ran into some fashionistas. Just seems weird for someone to go out of their way to comment on it, at least in English Canada.
Then again, the Winnipeg Jets just unveiled their new logos, all 3 of which have the maple leaf prominently displayed. To me, this is another example of how we're slowly, finally embracing a bit of patriotic display in this country. Yet half the forums on the Internet are full of people asking why we'd put a maple leaf on a hockey jersey. So I dunno.
I definitely know what you're saying - Canadians historically have been and still are one of the least likely people to really self-identify with their country's symbols. Keep in mind we've only had our own flag for barely 2 generations, and we're some of the most humble people on the planet. Not really sure why that is - I'm personally fiercely patriotic. To each their own eh.