Use of space
The use of negative (roads, town squares etc) and positive space (structures) looks very convincing to me. The roads themselves look organic and I love the little alleys as well.
Colour and line
I really like the range of colours you have used to suggest contours and the fractally edges to them - did you do those by hand using a custom brush? My only very minor, purely subjective, nitpick is that the land colours look slightly more desaturated than the sea colours. Below is a hypsometric colour pallete I sometimes use which you may find useful:
I also really like the black outline you use only to the right of the lakes and coastlines to indicate the direction of light. The building textures fit really well with the scale you've employed.
Looks great! No comments.
Use the burn tool to suggest shadow under the woods or maybe a drop shadow - not sure if drop shadow would be too obvious. Also the same to the right hand side of the walls to be consistant with the light direction. You might also want to use a complimentry colour to that of the background in your text so it will stand out more (but that's a matter of taste). More suggestions of vegetation (like in the north eastern corner of the city) would look good too perhaps around the lake.
I would love to see a tutorial as to how you go about producing your maps, they're very professional.
I didn't take too well to the scribbly map...it looked a bit too much like a photoshop filter had been applied to it whereas with the first one it looked much more hand painted.