I am designing this city as pretty much the entire world for a thieving sandbox for DnD 4e. It is set to be a rather large city built around a very active port. The city is basically split in two halves by a river, both halves of town will be quite different in terms of game-play (the lower half will have a very structured guild, while the top half will be controlled by a very loose guild.)

I plan on having a basic map with just sections (similar to the second attached picture) and also a map that shows every single building. To keep with the theme of the game I am going to try for a hand drawn style and pretty much draw the whole thing with my tablet in GIMP.

Any C&C is greatly appreciated. Whether you love it or hate it, tell me why. The goal isn't to protect my feelings and boost my ego, the goal is to make something great.

Here is my preliminary sketch:
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And here is the beginnings of me laying out the different sectors and main roads of the city:
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