I've lived in MTL, Toronto, and Vancouver.
Montreal is the most affordable, the city does a lot of cool cultural stuff, there are lots of cool women out there, and the skate scene is pretty amazing. But knowing French is kind of a must. You can get by as an Anglo-phone, but you are going to miss out on a lot. Also, the healthcare in MTL sucks, the winters are hard, and the Quebec government sucks.
Vancouver is fucking amazing in terms of weather, the parks are super fun, Menu is a pretty cool shop, and BC's nature is amazing and the healthcare is the best in Canada (I think). But, Vancouver is like a pretty girl with no personality. There is little culture there and the people are tech bro as fuck.
Toronto is just a mix between the two cities, but its one highlight is being able to experience so many cultures in a single place. I miss the Polish part of town, the Russian part of town, the Ukrainian part of town, the Dutch areas outside of the city, the Turkish area, and so on. Toronto's multiculturalism is so much fun. However, I feel Toronto lost a key part of its skate culture when Baitshop decided to close down its retail location.