The province has a fairly good GIS open data site at https://www.javacoeapp.lrc.gov.on.ca/geonetwork/sr...
which has been my go too for much of my mapping data in Ontario recently.
It seems there is Lidar data for much of the province but they've skipped the GTA.
However, if you search for "Toronto DEM" it comes up with some data based on a 2002 orthophotography survey. Not sure if this is the same or different from what Ian was able to provide.
Take a look at that data and see what you can do with it. I tend to open this stuff in QGIS and process it there to get something I can put into OCAD georeferenced to the same coordinate system as all my other data. If you need me to do some of that let me know.
Also, my sisters boyfriend works in GIS in southern Ontario so if you like I can ask and see if he knows anything about Toronto data.
Re photos: There's a tool called SASplanet (http://sasplanet.software.informer.com/14.12/
) that allows you to clip out georeferenced photos from a variety of sources such as bing. Theoretically it can also do Google but it always gives me an error when I try to view google photos. I then load that exported file into QGIS and do an export of that QGIS layer with the appropriate coordinate system. I've tried a couple of times to do it without the intermediate QGIS step and there's always been some issue with it. Unfortunately, I don't know enough about georeferencing and coordinate systems and the like to provide much insight beyond saying it doesn't work.