I decided to pick up on one of my older maps (one of my first, in fact) that I never really finished. I tried colouring it once before, but I had no idea how to tackle it.
Here's a new attempt, with much taken from Torstan's tutorials.

The old version:
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And how it looks at the moment:
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Shading the rock that this town is on. Black and white (brush pressure sensitivy set to pen pressure) on two overlay layers to build up the core shadows and highlights.