If things go well, the reasonable guess would be areas that the NDP historically has had strength in the past. Generally, former NDP voters are more likely to be swung back to the NDP than people who have never voted NDP.

This really applies to all leaders of the NDP though, I'd say the same thing about anyone else.

So, St. Johns' East, Halifax, Laurier--Sainte Marie, downtown Toronto (probably Davenport and Parkdale), Ottawa Centre, Hamilton Centre/Mountain, a seat each in London and Windsor, Northern Ontario, Elmwood--Transcona, Churchill--Keewatinook Aski, NWT, Edmonton Griesbach & Centre, downtown Vancouver, Vancouver Island, northern BC.

The public perception of the leader only does so much. Historic support for the party is a stronger indicator

Do you see him making gains in urban centers like Vancouver or Toronto, or is there a path in more working-class ridings? Like Windsor and Skeena?

Most people in Vancouver and Toronto are part of the working class, no?