@Paladin-Cleric of Awesome Looks like you've got a good start there. You've got a few places where shadows are missing/inconsistent, mainly around the castle and the buildings that have shadows going into the walls, so if you're not using a script to do them, I would fix those. Additionally, what I think you're really missing is greater detail. Things like broken bricks, cracked roads and especially plants and nature things around the more natural parts of the city. Also, it may just be me but I feel like the wooden fences inside the city walls are a bit off, I'd replace them with one of the other ones. Overall I really like the layout you've got going on, you just gotta fill in all the empty space with detail so the map really pops.
Completely unrelated, this is part of the hills that surrounds a town I've been working on. I'm pretty happy with how it looks but I'm a bit concerned that there's too much going on at any given time. Thoughts?