@transit - Public Transit in Toronto is largely a shambles (and the newer the project, the less likely it will work as promised) - a patchwork of political vanity projects with often few real benefits, and with a provincial government that resents anything that seen as an inconvenience to private vehicles.
Possibly the last forward-thinking move for transit in Toronto was the building of the Bloor St Viaduct in 1918, where a second level was included for a subway, which was still 50 years away.