I was in Montreal for 4 years before moving to SF so maybe I can help a little. I've also been using uber from the moment they started and have used it in multiple cities.
Apart from the basic benefit of not having to get your wallet out, I'd say it's the option of choosing between different type of rides that I like the most. In SF via uber we can get taxis, uberx (basically Lyft, some drivers do both), black cars, and SUVs.
In Montreal I don't remember ever getting a black car, but I was student at ÉTS so maybe that's a moot point :)
For your last question, SF has a developed taxi network but it's really bad. Montréal in that regard is much better, but maybe when leaving the bar at 3AM you'd rather get a black car to take you home rather than a taxi from Hochelag, and uber would make that really easy for you.
It's true that Montreal payment is annoying. Many don't take credit cards. I know how to work the system now, but it took a bit of getting used to. Would be much more awkward for 3 AM cabs.
Apart from the basic benefit of not having to get your wallet out, I'd say it's the option of choosing between different type of rides that I like the most. In SF via uber we can get taxis, uberx (basically Lyft, some drivers do both), black cars, and SUVs.
In Montreal I don't remember ever getting a black car, but I was student at ÉTS so maybe that's a moot point :)
For your last question, SF has a developed taxi network but it's really bad. Montréal in that regard is much better, but maybe when leaving the bar at 3AM you'd rather get a black car to take you home rather than a taxi from Hochelag, and uber would make that really easy for you.