I've been playing around with different tutorials, as a starting point, so it was inevitable that I got to Torq's Mountain Technique Using Wilbur and Gimp. I never just follow the tutorial unquestioningly though, so I tweaked some of the steps and added a few others. So far this is my result;

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What I am having a real hard time with is coming up with a city marker concept that is not just the traditional dots, circles, stars, etc. I've tried small-scale mosaic filters, but I either have to make the cities
too large for the scale or too small to get any real detail from them. Any suggestions?