The only thing that I had in mind when I started this was to experiment with a regional style. I had done continents in the satellite style for years and over the summer started doing cities so that left the in-between regional map (I haven't even thought about doing encounter maps).
Starting with my normal (artistic-satellite) style this began to take on a new look when I first put the rivers in. They looked a bit "cartoony" or "video gamey" to me and that, in turn, led to the cities being even more so. Then I put down my icons to designate areas of interest. When I started labeling I didn't have anything particular in mind until I had an idea to do something which I had never seen but thought might be cool...big ole carved stone text for the labels similar to looking at Stonehenge in an ISO view. 3d programs really test my pea brain so I tried to do something similar entirely within Photoshop. Having these big carved-stone looking city names I decided to redo the cities in a more isometric look, again staying entirely within Photoshop. Having faux 3d cities names and cities I had to redo the icons for the areas of interest and luckily I had some old Google SketchUp images to import.
I'm really happy with how it turned out and hope you all like it as well.