I like the dichotomy your trying to achieve between north and south. But, your map really lacks a since of scale. If those pencil marks of thin roads represent your small alleys, which would be about 5ft wide, then your great roads appear to be 500ft across. I think you have too many and too wide of bridges. Crossing a river that wide is a major undertaking. I would be surprised if a major medieval town had two bridges over a river that wide.

Unless there is a legal reason in place, some of the north would be cheap wood construction, and some of the south would be expensive stone.