Help Remaking a Regional "Painted" Map

[Tancread]

I am pretty sure that small map clip you have there is a Games Workshop map which makes Happimess's tutorial that exact thing for you to have a look at. His map in the tutorial is another part of the GW world, but it is exactly the same style.

[landorl]

A graphics tablet would be your best friend for doing the mountains. You could also hand draw the entire map and then scan it in, but personally, I have never had the best results with scanned maps. Of course I have a fairly cheap scanner