In general, precipitation seems to be one of the tougher areas, especially as it can be very localized. With snow, you then also throw in rain/snow lines which, where I live in New England, are very commonly somewhere within the greater Metro area.
But in the big picture sense, and for things like hurricanes, forecasting has improved a lot. It's unlikely we'd be caught by surprise today as happened with the Blizzard of '78 when massive numbers of cars got stuck on the highway and had to be abandoned or people were stuck at their offices for a week. (The weather events still occur of course but they're less likely to catch people unprepared.)
That happened in Chicago in 2011 - a blizzard caused hundreds of cars to get stuck on South Shore Drive. I'm not sure if it wasn't warned or people were just stubborn.
It's probably less true than it used to be but, for years, a lot of people in Boston were really paranoid about big snow storms. Everyone knew someone or at least knew someone who knew someone who had be evacuated from Route 128 or slept in their office for a week.
About a decade later a friend of mine moved to Boston and she once told me that she had never seen a northern city where people took off home from work at the first snowflake the way they did in the Boston area.
But in the big picture sense, and for things like hurricanes, forecasting has improved a lot. It's unlikely we'd be caught by surprise today as happened with the Blizzard of '78 when massive numbers of cars got stuck on the highway and had to be abandoned or people were stuck at their offices for a week. (The weather events still occur of course but they're less likely to catch people unprepared.)