There is also the possibility that one or more of the five passengers will be randomly selected for a COVID test on arrival. This is a pretty fast process, but is another thing that could get in your way.

I think what it comes down to is the mental state of the travelers.

Let's say something goes wrong and you have to wait for another flight. Will any of the travelers melt down over it? Will there be a CBC article about how one of you (ideally a veteran, or someone with cancer who finally was able to go on vacation, possibly with a puppy waiting at hone for them) was "abandoned by AC at YYZ"?

If the answer is no, you are all pretty chill, then book the short connection, understanding that it may not work out.

But if any of you much prefer the certainty of which flights they will be on, you might find a boring but drama-free longer connection is a more enjoyable ending to your vacation.