In continuation of THIS THREAD, which is where I was seeking general answers and it morphed into getting feedback on my map (for a story and created following Gidde's tutorial on hand-drawing maps in GIMP). So here's an official WIP thread. What I've done so far is as follows:

Map 1.0:
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Name:	Map test.jpg 
Views:	68 
Size:	1.45 MB 
ID:	83664

Map 1.1:
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Name:	Map test 1.1.jpg 
Views:	66 
Size:	1.47 MB 
ID:	83663

Map 1.2:
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Name:	Map test 1.2.jpg 
Views:	174 
Size:	2.28 MB 
ID:	83662

At this point, I am considering beginning adding towns/cities and roads, unless anyone has more suggestions for me to try out.