Hey Lupin, just saw this post, and since I'm also in Ontario, I can tell you that my upstairs windows were even more low-tech than yours. Mine were just a fixed sash at the top, and a sliding sash at the bottom. No stay pins, no weatherstripping, no ropes, pulleys, chains, springs, or anything. Literally just a frame in a track. This is the type of window that you'd just prop-up with a stick, or if you want to be fancy, they actually had special sticks you could use (sort of like a large notched saw blade) to adjust the height of the opening. Of course I can't find a photo but I'm sure I've seen some before.
I have no idea if the first floor windows were also like this since they were scrapped before I bought the house.