I've lived in Montreal for 22 years and I can comfortably say that Montreal is an amazing city. Probably one of the best in the world. But holy fuck does the province suck ass. 40%+ income tax, 15% sales tax, tax de bienvenu, tax over tax, etc. only to get treated like a second class citizen if I start a conversation with "Hi" instead of "Bonjour" with the wrong person.
The weather, the healthcare system and the infrastructure are by far the most miserable things about the city. The rest is fantastic. But those 3 together make it a rough pill to swallow sometimes.