For a future late spring or summer, I'm thinking about a weekend vacation to Montreal:

Get a free bonus 1-2 Free day from referring someone to National's Emerald Club.

Day 1, Friday

Drive one-way JFK to downtown Montreal, $9 NY CDW & pre-pay for gas to avoid the higher prices in Canada. Stay overnight at a hotel with free parking, probably near YUL. I'm thinking of an opaque booking with Hotwire, since retail rates seem to be much more than airport hotels tend to be in the US.

Day 2, Saturday

Drive to National's neighborhood store in downtown Montreal & return the car. Take a guided tour of the city. Possibly switch to a hotel downtown, since the car will be gone and free parking will no longer be an issue. If the cost is too high, take the bus back to the peripheral hotel.

Day 3, Sunday & part of Day 4, Monday

Take more tours.

Late afternoon on Day 4, Monday

Take the bus to YUL, and fly back to the NY area for free using credit card points.

My questions are:

Has anyone done anything like this, and if so, how did it go?

To cross into Canada, I would need a paper rental contract and my US passport. Would I also need anything else for the rental car from National at JFK, such as its registration and/or a Canadian insurance card?

I've done a Hotwire opaque rate in a Boston suburb, and everything was fine. Are there any quirks to the process or outcome in using it for hotels in Canada?

How much French would be appropriate to learn? I don't expect to visit another country and assume that everyone speaks my language. I would respect the dominant culture by attempting to speak to the local people in French.

However, conversational proficiency is obviously easier and faster to learn than real depth. I presume this would be fine for routine social interactions. As in, if someone on the street says hello in French, and I don't answer, the other person might assume it's because I'm rude, rather than because I didn't understand.

But if there are unforeseen issues crossing into Quebec, returning the car, inexplicably getting a receipt different from the total price on my rental confirmation, etc., in other words, things that require thinking about and explaining more complicated things, and in a language I don't know very well, that could be a problem. Would a pocket dictionary, electronic translator, etc. be useful to take?

Is there a list of guided tours offered at Montreal landmarks in English? I don't think Montreal has a Ducks-style tour, or a trolley one.

Other relevant, helpful suggestions are also welcome.