I think you're right about the blobs (im kinda thinking now they look like blood, eugh). If I may explain, my intention was to try and give a sense of scale and shape to the cities. I was afraid icons wouldn't quite convey the physicality i'm looking for. My grind comes from trying to convey the size, shape, and layout of a town or city simply and quickly. I may have to put more effort into that.
I really like your Dutchy of Normark map, Diamond. It makes me think that roads might be the key to deciding the design of and conveying a sense of my towns. Anybody know of any tips or tricks I should be aware of before I start my probably very time-consuming roadmapping of a continent?