Aerial Photographs (2017) (toronto.ca)

Toronto has amazing archive from back then! Regarding the aerials, the first photos describes what elderly people used to tell me "Toronto back then was just plain fields". Same goes for other big cities probably. Thanks!

Nice.

Would it be possible to GIS these or join them into a google map style interface ?

If you found that interesting, UCSB has a huge free database that covers California and a few areas outside of CA, mostly on the west coast: https://mil.library.ucsb.edu/ap_indexes/FrameFinder/