I decided I'd post pictures as I experiment and move further along here. So far I've finished just the base of the map (landmass & major bodies of water). Put in some border and coastal wave details - but still have yet to do any terrain, landmarks, cities, rivers, roadways, etc. This will be the surface version of the map - there will also be an underworld version of it after I finish this one. Hope you enjoy. Any tips, tricks, advice or even general comments would be greatly appreciated! Thanks!

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Name:	CotFS World Map v1.jpg 
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That's how far I made it in my first night (about 6 hours worth of work). It's tedious, but it's coming along. Trying to find the right brush sets for terrain that will match the style (likely be making most of them from scratch).