I naively used to think that the surface parking lots found in the downtown were the result of Toronto being a relatively young city (ie. more undeveloped land). Imagine my surprise when i realized that they're actually the product the demolition of older building stock, incentivized by lower carrying costs of surface parking lots. So many relics lost!
Urban cores back then were far more dense, pedestrian-oriented and granular, and you'd only really find undeveloped lots in the newer suburban districts due to the desirability of the walkable proximity that came with central locations.
Definitely a huge shame that beyond the few impoverished towns that went through the rich-poor-rich cycle (that couldn't afford/were overlooked for urban renewal projects at the right time) and huge cities like NY or Philadephia (that were difficult to redevelop) that there's so few intact downtown cores around.
There were also many buildings that were in various advanced stages of decay back then, which made it easier to justify their demolition- the same thing still happens nowadays, unfortunately, which is why I think that heritage preservation should be based around what 'could be', instead of what 'remains there'.
Yes, up to a point. Clearly having a building @ Front & Simcoe is MUCH better than a parking lot but ...
..300 Front St. The high-rise garbage put up these days will stay with us far longer than garbage put up in the past.