Re-posting here, just for a thread of its very own. After tinkering with Blender for a 3D map, and Photoshop for a brush-based map, I wondered; Can you put these two approaches together? And then I ran across this, How to fake a forest in Blender, a two-part tutorial.

This uses Blender's 'particle system' in a way where a single 2D tree tree image (or a variety of trees) can be duplicated and scattered with various sizes across your map. You can paint with brush tools to define forest areas, or modify the density of trees, and ultimately fine-tune with individual edits.

Manually duplicating a few trees
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Applying the particle system. Look at the little tiny trees!
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Attempting some paper texture displacement. (following How to make a procedural paper texture)
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Ramping up to 8,000 trees
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The full area. Trying to carve a path through the woods. There's probably a less-is-more lesson in here somewhere, but I don't want to hear it yet, I'm having fun
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To be continued... So far, this was done with one tree from the Widman Brush set from KMAlexander (thanks again, for all of these), and there's a bunch more to explore.
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Remains to be seen is if the '2.5D' illusion works for all the other kinds of map elements (individual structures, settlements, etc.)? But for now, it's been fun to try cultivating some forests from the trees. I'm curious as to what folks think. It seems to look good at certain scales. Bit heavy on the shadows? Need more definite boundaries? Can this open up entirely new realms of forest-creating tedium?

and thanks Tiana for your feedback! This could become a tutorial to share what seems to work