I like this one (oh, sure, welcome aboard!).
Probably the "cliff" is the only element i would definitely change, because is somehow difficult to understand.
About the city plan, however, i think we need to focus on terrain: where the city was built? If i make a comparison between Turin, Rome and Siena, i see that turin was made by romans on flat terrain, with straight roads, intesecting at 90 degrees; Rome grew around the seven hillls and the Tevere, and you see a pretty complex urban structure, the more recent part rational and the older... Well, a mess :d ; and Siena, is a tipical middleage italian hill settlement, whose streets are disposed like irregular onion rings around the central place (piazza del campo).

So, what's the story of your town? Where is it?
Knowing the answers you will understand if there are "flaws" in the layout!

I wait for further development