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Finally, FINALLY! Most of the city is done. All the larger blocks are finished. I just need to do the rest of the city walls, a graveyard and the rock that the castle is built on (with a few houses here and there).
I'm not sure if I will do the writing by hand or in photoshop. It's so easy to mess up by hand, but I wonder if it will have a hand-made look if I do it digitally. Maybe I can apply some effects to make it work, but that's something I'll need to research a bit first.

Overall, I'm pretty happy with the way it looks so far. My biggest problem with it is that the city still looks flat. I tried use the advice I've been given, but I still forgot from time to time. And I should have made some buildings overlap at the back of the city, but was to concerned that the streets wouldn't be visible enough. I hope I can apply some shading to correct it a bit after scanning. We'll see