In both Canada and the US each "side" loves ratcheting up government power against what they perceive as their political enemies. It's going to end in tears.
That just means the conservatives can never be allowed to win elections...to protect Democracy!
Recently we've seen a functional alliance of those on the bottom half of the diagram.
That's what happens when there is change in the world. Conservatives resist change, but change often has a momentum of it's own.
The world has changed a lot recently. TV brought everyone together. Transportation made the world smaller place. The internet and social networks gave everyone a voice. These are all game changers. For better and worse. We can't un-invent all that stuff.
The reason older people tend to be conservative is that they are used to the way things were when they grew up. They don't like the changes. They want the good old days back.
Young people don't have these notions about the good old days, they weren't around. They started off with a different view of things. The Overton Window moves with them. Progress ratchets, as you said.
p.s. None of this implies that I endorse how the protests were handled. I'm all for democracy and 100% against authoritarians - whether they are communists or fascists or whatever else.