I have photos of a 'real' smallscale city at my disposal, which has the basic houses in simple carton, paper and other stuff, and some old drawings. From that I am supposed to make something that is around 1600-1700, so very late actually. Due to the amount I get paid and the time I can spend on this before deadline, the houses cannot be very elaborate unfortunately. After this I will probably make some really fine medieval houses (at least attempt to). These are simple, and only to be viewed from a distance. And the historian isn't providing me with all the details I need of the particular houses, so it's a lot of guess work.
I made some really lowpoly people to lessen the streets emptiness, and will probably mask the roadsides (along the houses) and add some populations of crates, tables and heaps of 'stuff'.