Being your first trip to Montreal, I understand you being a bit flustered by what the city has to offer. My first time there, a few months ago, I was enamoured by what to me felt like this charming package of a city. After going back 4 more times since, I have realized that under the surface, Montreal is in such a colossal mess that it makes all the problems we may have with Ford seem like a joke.
The subway system is both architecturally and geographically better. The stations are beautiful (Montreal does art with concrete) and it covers the central area very well, branching only marginally into the suburbs (although recent extensions and planned extensions will change this). Had Toronto received its subway around the same time (late 60s, early 70s) we'd have an entire subway made of Spadina-esque stations. Imagine Dupont, Eglinton West and St Clair West duplicated for our entire network. Functionally, it is a disaster. Frequencies are horrible (waited nearly 10 minutes on a Friday evening for a train to take me from McGill to Beaudry), the trains are narrow, poorly laid out and HOT! Jesus, it was worse than the NYC subway. Also, those must be the noisiest electric trains I've ever heard, it's like standing next to a GO locomotive. You cannot hear the person next to you shout over the noise these things make when coming or leaving a station.
The streets are better in select areas; the key word being select. The Quartier Internationale (where Square Victoria is) and some of their principal downtown high streets have impeccable paving, lighting and decoration. Go outside of those areas, to regular streets or downtown side streets and the result is terrible. Potholes everywhere, cracked sidewalks that could swallow a distracted pedestrian and graffiti, graffiti everywhere. Not the artsy kind, but tagging of the worst kind. I guess you could say Montreal is a city of extremes. Schizophrenic but it all comes together in a tolerable whole.
Architecture... Now this is my favourite part. Obviously Montreal wins HANDS DOWN in the historic department. The old city is beautiful, bit Main Street Disneyland-ish, but serves its purpose for gawking tourists. There are beautiful squares strewn about the city, and this I blame on history. Toronto was built on the English model, which is rather little parks instead of squares. Montreal had the continental model, which favoured squares over parks. I personally love Montreal's squares, but I also love Toronto's parks dotting the entire city. I do wish we had a formal square in the European model, not that garish mess at Dundas and Yonge. Can't have everything I guess. In the modern department, I have always been a fan of Montreal's PoMo towers (now there's a skyline dominated by that style). 1000 de la Gauchetiere is one of my favourite skyscrapers in the country, and the modernist Tour de la Bourse is a close second. Toronto clearly wins this category hands down - again, Toronto's economy and ambitious growth was trumping Montreal since the early 40s, it just took 30 more years to formally overtake it. One thing I did notice is the incredible amount of abandoned, dilapidated buildings all around Montreal's downtown. Some looked ready to collapse, completely covered in postering and plywood. Also a large amount of empty storefronts; something you don't see very often in Toronto. Street life was great, not as overbearing and busy as Toronto's, but that right mix that makes it both enjoyable and gives you the feeling of being in a big metropolis.
In terms of people, I can't tell the difference between an inner city Torontonian, and the Montrealers I encountered. Both seem into the same things, frequent similar establishments but just do it in a different language. That whole latin blood passion thing is a whole lot of bullcrap. Quebecers are purebred North Americans, and aside from speaking French, they couldn't behave more similarly to the rest of us if they tried. Montreal has an identity which is tied to the Quebec identity. That is primarily through Montreal's role as the metropolis of a unique cultural group with unique needs and a unique language (in our geographic context). Having their media, film industry, music etc, being local in focus makes Montreal seem more like a 'place' rather than a relay tower as Toronto is. There is nothing we can do about this, so no point in delving.
Culturally, both are similar in what is offered. Vibrant arts scene, music scene, both have good museums (although Toronto has the blockbuster museums Montreal lacks) and the collections of the ROM and AGO far outshine anything they have. Montreal has this vibrant local scene which Toronto is slowly building; again this is tied into their role as being the metropolis of a distinct group, unlike Toronto - however we are slowly building up our own local scene and as the years progress this rift will close.
Economically, you can tell Montreal is still struggling with numerous macroeconomic indicators. Corruption in the construction industry and municipally makes development a hassle for well-intentioned developers and an easy sell to hacks who put up some of the most monstrous things I have ever seen in Canada. There is far less 'wealth' in the city (if that makes any sense) but it definitely leaves an impression to someone from a city overflowing with it. The city seems to do its thing well, and they are satisfied in being a great second city (and a great Barcelona they would be). Something that truly explains Montreal's financial sector is affixed on the lobby of the Tour de la Bourse: "Bourse de Montreal, a division of the TMX Group". So many jobs and prestige was lost to Toronto that Montreal's financial sector definitely has that second fiddle syndrome. I find it ironic that BMO's legal headquarters on St. Jacques (legal, not operational as that is in Toronto) have the old M-Bar logo on top. The last time I saw that logo anywhere in Toronto must have been at least pre-2005.
To sum it up, I really like Montreal, well enough that I wouldn't find it an inconvenience to live there. I'd quite like it actually. But its relative stagnation in regards to Toronto's dynamic changes, both architecturally and economically, makes me think I would get bored fairly quickly. I like the quick changes in Toronto shaping it to be one of the major alpha cities of the planet. I just turned down a job in Montreal because I'd rather focus on finding the right job in Toronto, where I'd rather start a career, but if I could be reassigned to Montreal for a few years I would definitely not find it an imposition.
I'm glad you enjoyed your time in the city, but after going back a few times, you realize that your first impressions were like feeling silicon breasts. Amazing at first, but then you see the scars and the whole just doesn't seem right anymore!