I've never thought of the Fort Osborne Barracks being so densely built up, but I guess it makes sense that it would be in 1921, so soon after the war.
One of those houses seen beyond the Barracks was the home of Archibald Wright, who owned basically all of Tuxedo and what became Assiniboine Park. The house is
still standing on Academy Road, and I think its original parts dates back to 1880 or even earlier.
Seeing these photos make me wonder how new residential development (long river lots subdivided and eventually filled in with houses) was paid for back then... Like, to fully service (even by 1920s standards) these thin strips of lots doesn't seem very efficient. Of course now these old gridded streetcar suburbs are all built up and viewed as a smart growth ideal, but I wonder how 'smart' it was to develop this way.