Maybe what I could do in future town maps is having roofts instead of just black blocks. I will admit it does give a nice simple style, still it lacks the feel of variety which I see when people have their roofts. I also notice a mistake I did. Well, mistake yes and no, it was a map I started at first just for some practice but then a friend wanted it for his D&D and the cliff was already fully drawn when he told me below is the ocean. Next time, having a port would be nice. With boats. It could be also the port is just one or two miles along the road, but honestly I can't see any logic in a space between the city, and the docks. I mean, obviously you want to protect your dock and your houses, so it would be illogical to separate them right?

Concerning the network of roads, having those circular plaza was actually a mean to have some main roads diverging from those simply going towards a gate. I think it gives some intelligent design behind the growth and spreading of houses. True enough, its not really representative of the Middle Ages since houses were added in an organic fashion, and smaller roads were more like shortcuts between the main roads, and then the secondary roads, until no more shortcuts could be added. At least if I remember well... I did alot of searching, but didn't find much to say research >.<...