First I'm not sure this concept is a legal entry for the challenge, if it isn't... somebody say so and I'll think of something else...
Second, this first post is REALLY REALLY early in what I'm thinking of doing (infact, I'm not entirely sure I've got the plan purely flushed out yet )
My idea is going to be that area where "the market" and the nicer residential district kinda meet in a better of town... cobblestone streets, lighting (un-added at this point)... and a mixture of grouped housing and largish estates... for some sections I'm using the shape as a land plot, and some I'm using the whole shape for a larger building...
I'm fairly slow at this, but I'll try to update my WIP as I go, and if the few maps both of areas and of individual buildings are any way to judge time... I'll probably be really close to the deadline.