For all its reputation, I'm not sure Boston is clearly a lot harder to drive in generally than a lot of San Francisco is--given Boston weather for maybe 8 months out of the year. However, after a big snowstorm (admittedly not much this year) it's a whole other game. And while it's easy to say just don't use self-driving if there's a snowstorm or if lanes are partially blocked by snow, that's not ultimately a driving system that can be depended on. And I guarantee people who maybe only drive a few dozen times a year in the worst conditions will be an absolute menace on the roads.
(And "just don't drive then" isn't an option for a lot of people in a lot of circumstances.)