Vancouver and Toronto both have a huge lack of freeways within the city boundaries due to NIMBY/resident activist movements over the past 20-50 years.
There is a stale proposal on the shelf for a 6 lane underground toll freeway from Pearson-running under Eglinton, then running south-east under the UP line by Black Creek continuing under the Gardiner, north east (with a tunnel access structure conveniently built over the Greenwood subway yards), and then continuing under the Go/VIA rail corridor until it joins up with the Guildwood Highway (2A) . It would be easy to build access points over the rail lines without leaving a scar in the urban fabric. The proposal calls for the project to be financed by the private sector.
https://dailyhive.com/toronto/toronto-tunnel-proposal-2017
I could see somthing similar in Vancouver with a west side highway and an east side (loop) highway with a connector under King Edward.
The West Side Highway would be tunneled under the West-East mall (Arbutus) traveling from Richmond and then linking up with the Granville Street Bridge.
An East Side (Loop) toll highway under the Millennium and Expo Lines would have a very easy tunnel access point around Boundary Rd and the Trans Canada Hwy as well as at Terminal and Main.
I imagine it would be easier to connect my 2 fantasy underground highways by tunneling under King Edward vs tunneling under Broadway.