OK, taking in all the feedback and posted responses to map submissions in the Paizo Open Call thread... http://www.cartographersguild.com/news/4092-paizo-open-call.html
I thought I'd still try and create a city map, an attempt anyway. I don't want to hand-draw the monster, and since we now know that Paizo doesn't want anything too realistic, yet they want to see viable rooflines. I chose to try a new method.
First I opened Nendo my easy 3D modeler and created a bunch of building shapes, mostly concerned with rooflines. Then I did a top view orthographic camera screen capture to produce my overhead map objects.
Below is a side view of the created 3D objects, then the top view, I used to create my objects with. The third image are the objects given some color and several steps to get individual buildings to play with.
As a small tut: first I imported the screen capture into Xara Xtreme. Then I rotated it to be more in line x and y for drawing rectangles and such. Then I began to create rectangles, circles, octogons to cover all the buildings in the screen capture. On the more complex buildings are more than one shape stacked.
Then a series of Combine Operations to get to where I needed to go next.
For complex structures consisting of more than one piece. I selected all pieces and performed an Arrange>Combine>Add Shapes to make the complex shape a single shape.
Once all the individual buildings were made into basic shapes, I selected all the objects (not the screen capture) and did a Arrange>Combine>Add Shapes to make all objects into a single shape (just temporary though.)
Then I selected the objects and the screen capture and did an Arrange>Combines>Intersect Shapes, which cut away all parts of the Screen capture that were not part of the selected building objects. Finally I performed an Arrange>Break Apart to separate the buildings into individual objects.
Now I went to the color bar at the bottom of the Xara screen, selected an individual object and applied a color fill, which still maintained the lineart rooflines. I moved the buildings a bit to show that they are individual objects now.
I plan to create about 50 more general building shapes. Then perhaps 20 specific buildings for bridges, temples, gatehouses, towers, palaces and such. The general buildings will be used over and over, though I may apply different colors to them so that seem not simple copies of other buildings. I will resize a few.
Once complete, I will create a separate street plan with defined roads, streets, and alleys as per Paizo's desire, and begin to populate the defined "city block" locations with the building objects.
I'm not saying this is my preferred city asthetic, but I'm trying to cater the art to what Paizo seems to want, at least from my point of view.
Of course I will create unique walls, gates, ports/piers, and higher ground areas before the work is done. I also plan to create a few statues, collonades, park areas, moats and perhaps some canals.
Anyway, just to experiment with a different style and create a city map, even if Paizo rules it out for different reasons (:?:) I'll give it a whirl.