1000 Bay is very overpriced IMO, unless you manage to scoop a high-floor unit that's facing the park, with an unobstructed view protected by the historical buildings. Also the Yorkville Plaza has a sort of nostalgia attached to it.
I find that the biggest differentiation between old and new condos would be square footage. The area where you put your shoes in Yesterday's condos is called a "Study" in Today's condos. In the older 1+dens, you could actually convert the den into a second bedroom. New condos, not so much...