Do the test on the seaway, I'm sure one 180% turn wont mean losing your ProTour contract. ... Do try and pick a day with light winds, differing wind speeds will make it harder to make both directions a constant block of similar effort.
I have a U-lock for the front wheel and the frame and I also use a cable that I bought 15$ for the back wheel. BIGLUFU Bike Security Steel Cable Lock, 4FT Braided Steel Cable with Loop End, 4-Digit Combination Bike Locks (Black Cable) https://www.amazon.ca/dp/B085ZVZYQ6/ref=cm_sw_r_cp_api_glt_i_BZGM5PTWEDRG8RY2W5KY?_encoding=UTF8&psc=1
I don't really have a recommendation. I only bought one 6 or 7 years ago and still use the same. I can't remember if it was MEC or Sport Expert but it's this model.
I went into a bit of detail on one of these rides with a new blog post.
The classic Chateauguay Valley (aka Haut-St-Laurent) road ride.
It is a favorite ride of mine with good roads (smooth clean dry scenic quiet), easy terrain and distance, and has Quebec's oldest covered bridge.
I crossed at the Hemmingford border crossing a few years back. They did make me go inside to check my US student visa, but that's been happening to me all the time no matter my means of transport. For going back to Canada, I recommend the Clarenceville crossing in Vermont. It's really tiny with practically no traffic.
Edit: Got the border crossing wrong: It's the Alburg one. Here's the route: https://www.strava.com/activities/63667095
There aren't many routes between Ottawa and Montreal.
I used komoot, and the most direct is by taking the 344 and the 148 on the Québec side, and cross into Ontario at Masson/Cumberland with the ferry and take the "Montreal Road"...
​
Using ridewithgps, it goes thrue Oka and cross with the ferry to Hudson. then the 342 road on to the Prescott-Russell recreational trail and then route 27 ...
The best tips I can give you:
J'utilise la meme phrase - "devoiler une roue". PVI, il y a une site qui donne des traductions contextuelles - context.reverso.net. Ca peut etre utile dans l'avenir.
For a shopping bike you could just use a commuter, with a back rack and add two of those or something alike that you can remove. Unless you are shopping for a big family you should be fine with this. I am thinking of doing that with my commuter myself.