Many homes in my area were built in the 50s, but the description you have provided is nonetheless relatively accurate. I live in one of the nicer area of the east end, and interestingly, some of the original bungalows (which by the way have
2-conductor electrical outlets but do not have knob-and-tube wiring) still have the original owners living in them.
It's a morbid death watch... Contractors are watching the nicer lots like hawks. As soon as one of these owners dies, the contractors descend to try to scoop it up to renovate for a flip. Or else a younger more professional couple comes in and scoops it up, and renovates it too, albeit for their own use.
As for family members affording them though... Some of the homes were willed to family members, but they often turned around and sold them anyway, since the lots are very good money, and there are cheaper places in Toronto to live.