Throughout history, getting water to a city has been a big challenge (it still is). Roman aqueducts would be a good example.
I'm not sure in what sense you are using "historic," but a major challenge to city planners in historic European cities has been how to create a modern city while preserving important historic and cultural aspects. For example, if you look at a map of the inner City of Vienna, you will see how the old city walls were torn down and replaced with a circular avenue containing important government and public buildings. Other cities (Palma de Mallorca, Spain would be an example) have retained their city walls (very popular with tourists), leaving traffic in the inner city in a very chaotic state.
The steep hills of San Francisco were a challenge for transportation, leading to the invention of the cable car.
I'm not sure in what sense you are using "historic," but a major challenge to city planners in historic European cities has been how to create a modern city while preserving important historic and cultural aspects. For example, if you look at a map of the inner City of Vienna, you will see how the old city walls were torn down and replaced with a circular avenue containing important government and public buildings. Other cities (Palma de Mallorca, Spain would be an example) have retained their city walls (very popular with tourists), leaving traffic in the inner city in a very chaotic state.
The steep hills of San Francisco were a challenge for transportation, leading to the invention of the cable car.