I've have been searching for a long long time for a way to freehand topography in a fashion that I feel is believable, attractive, doens't require topo data, and above all: fast. The other night I decided to try yet again and finally, finally, hit upon the right combination of layer effects, textures, transparencies, ink colors, brush type and painting technique to give me the effect I had been searching for.
I wanted to make an actual map, and chose the wonderfully horrible GM's map from the webcomic Chainmail Bikini. For the record, here's the before.

Here is an evening's work. This was amazingly fast. I had already generated textures for things like forest and desert. Most of the time was spent refining the mountain technique. The labels took a bit more time. There's a lot more tweaking and fine tuning I would do if this were a production map, but it was a very satisfying exercise.


The thumbnails below show the map without words, just the landforms, and finally the topo layer without any effects, so that the actual brushstrokes needed to create the mountains can be seen. I had to place the last in front of a pure black background layer, since the brush strokes are very light and not easily seen against white. The final map has a duplicate of this layer set to 50% multiply to enrich the shadows.


Map without labels


Landforms only


Landform layer without effects