Buried utilities versus aerial infrastructure.
As a retired Bell engineering manager whose duties included the design of facilities to be placed in new subdivisions and rural applications as well as urban renewal projects I know a thing or two about all those poles and wires that blot out the sun in some locations.
1960 was indeed a watershed year that saw the trend towards building less aerial infrastructure and more buried plant, both Bell and Hydro and later Cable TV in all three scenarios.
In new subdivisions the parties shared the same trench and lateral run-offs to the homes, all the digging was done by machine and there were no driveways or sidewalks in the way. The ongoing advantage of fewer storm or other damage was a sweetener.
Rural locations were reinforced by placing buried cable in the boulevard/ditch instead of adding another cable to a pole line that was possibly too far gone to stand the strain of another cable. The cable was placed by one or more bulldozers that forced a plowshare down 3 feet and laid the cable through it. This method was a little less than exact in the route of the train and the cable it laid was not all that straight and parallel to the fence line as designed . A right of way for a second cable 5 or 10 years later was rarely forthcoming from the municipality so it was back to poles and aerial construction.
Rebuilding aerial plant in the urban environment poses many problems. A lot of downtown Toronto Telephone and Cable service was originally placed in back lanes on poles, the Hydro service was and still is in the front street. Buried front street construction to replace aged or inadequate aerial services would be incredibly expensive for two reasons. The shared trench location in the boulevard area usually assigned to such utilities is about 12 feet back of the curb on most inner city street profiles, take a look out your window at that location. I bet it is full of trees ,gardens, driveways, parking pads etc, the City requires contractors to tunnel these features rather than machine cut and fill. To access the same point on your home that your meter or telephone/cable service wire enters is probably a bigger nightmare than the trench down the street.
Bottom line, too expensive and intrusive to private property owners. Imagine one home owner on the street who refuses entry to their property , and he or she is there believe me, and the entire project is dead in the water.