In the meantime, I did come across this great aerial photograph showing the area in 1957. The triangular plot of land in the upper left is where Roger Wilco was built in about 1960, and would become The Square. At the center right, you can also see the long-gone West Novato Elementary School.
Also shown in the detail below is Gustafson Court, the street I grew up on. My parents moved into the house around 1963-64, and I remember construction just beginning then on "Pleasant Valley 44," the development on Center Road, west of Sutro. San Marin High School was just being built at the time. This picture shows the area 6-7 years before that.