Well, I’m still working on this map and finally making some real progress towards a completed draft. The image above is a top-down parallel projection view from within SketchUp, with all the buildings redrawn to fit within the new walls & towers layout. I increased the size of the Royal Palace and the walls around it (on the inside of the town), and I drew in entirely new building footprint shapes within the Royal Palace district itself, for the most part. At the moment, the only thing missing is the Tartarus Prison (other than the terrain, which I’ll be adding in by hand during the final pass). I’ve been having some trouble placing it just right in Sketchup, and since most of the prison itself is actually underground, I think I may just set it up once I get the map into Photoshop for tweaking.
I still plan on printing out the map and tracing over it by hand in pen to get the best hand-drawn quality for the lines. Below is an idea of the town in parallel projection (again, just a SketchUp screenshot):
The colors in both these images are just part of the SkU style I selected to make the images more readable. The final colors will be more in keeping with the 17th century style of the maps referenced by the client.