Toronto winters can still get bad, delays can and absolutely will occur on surface sections. It is entirely within the realm of possibility that you get to a station right as a tram leaves, and you have to wait up to 10m for the next one to arrive. Heck, even 5m can be rough for some people.
Iirc the original plan in Transit City would've been to have either full shelters, or at least heat lamps along the platform that can be used to keep warm. I don't remember the specifics, but I think it was value engineered out of the plan sometime around when Metrolinx took over.