Hello David,
In the Netherlands we have a website where one can compare all known maps made during the past 200 years (plus aerial photos where available) with each other. So it enables someone to see a ca. 1944 map and compare it with a current map. Then, with the aid of Google street view one even can get a current view of the surroundings. See this thread for an example:
http://www.mapleleafup.net/forums/sh...176#post289176
The hardest part is finding the clues on where to look on the map. In the case of the Fort Garry Horse photos the road signs helped tremendously. For the case above I have asked the help of a local historian. Let’s see what he can come up with and then try to make the then & now photo.
Thanks for your interest,