I've been tinkering around with the exact same idea with Chicago data. Most of the bungalow areas or "streetcar suburbs" have evolved into neighborhoods in the city. But since 1950, many of the west and south side have been hammered with the removal of the street cars and the highways cutting them off from the rest of the city.

If the previous land values and usages can be shown, I believe a compelling argument can be made to show which areas are ripe for transit increase, and they will then show the most bang for the buck.