A funny thing happened on the way to GIMP...

I started the map with the general idea that the sun was coming out of the southwest corner (lower left) of the map, so many of the roofs have the north/east edge lined in more shadow. Most of the building shadows were added after the inked version was scanned in, and I think maybe some bolder shadows will help as you noted - I think I was a little nervous to shade over that much of the city, but I'm going to give it a whirl! It'll be on its own layer, so not hard to undo.

Thanks again for the continued feedback, I really appreciate it.

Quote Originally Posted by XCali View Post
If you have your MAIN direction of light figured out, then throw a big shadow on the side the cliff faces away from the sun(Be bold with the shadow, a hardly visible shadow won't work as well). And add a darker shadow closer to the bottom edge of it to make it pop even more(this is not a broad shadow. It is a core shadow. Basically a shadow that is somewhere that is the least amount of light getting there.)
Highlight on the cliff FACING the sun can really unite the effect of a cliff standing above the river.

Hope this helps