I feel like San Francisco is a good progression - still generally good weather, but much more crowded, more traffic, more special cases, pedestrians and bikes, one-way roads, topography, limited visibility due to hills and no-setback buildings, construction, buses, etc. It's a significant leap in urban complexity, probably greater than 98% of the rest of the USA.
Regarding the weather, lots of people have mentioned snow, but much of the Midwest, Northeast, and especially the South can have sudden torrential rain. I haven't researched it but I would guess that a Florida rainstorm would be hard for both radar and visual guidance. I predict their next city will be Orlando, in partnership with Disney. Then somewhere like Boston (harder - older street pattern and more snow) or Philadelphia (easier). Each of those 3 would "unlock" new territory they can cover. I predict that NYC will be one of the last areas "unlocked".