I like this map a lot. But.
For the most part, I was agreeing with THW, but.. I can see where you were trying for the slope, I think... and when I isolated that, I could see where those other issues came from...
Here's what I saw (and if I'm wrong, just ignore this whole post)
(Excuse the ugliness, I was going for clarity, not looks)
I marked out the cliffs/hills as well as I could see them through the texture (and I do agree, here, the texture, as is, is not right for this map). That told me how the ground was slanting. I tried to trace the main road (big red line) from the original city at the bottom, up to the top... and I hit a wall. You'd need stairs or a bridge/ramp/something to get up those cliffs if they are meant to be as marked. From the angle at which I *seem* to be viewing the slope, The road would (whichever method you use of reaching the top) seem to emerge at a different point. I started the new section of road there. Repeat at the top.
I can see how it would be easy to fix all that (again, if I'm right about your mountain) and even though each SHELF is larger than it would be (in comparison to the cliff faces) on a typical mountain, you could pull it off. But the angle, again, at which I see the slope, means that you would be viewing the walls from the same angle. I started trying to see where your walls would angle, and did fine up until I hit the cliff.
Now, if the city was originally at the base of the mountain, the wall would end at the cliff. Then, you say, it grew. The logical progression would be either to let the mountain itself be the rest of your wall, or to begin building a new wall on the shelf. If you have to angle it down the cliff, it would be really hard to draw (because the cliff face is so short).
And the perspective of the walls would mean you'd need to show the buildings the same way.
IF that's what you were going for with those darker areas I took to be the cliff faces.
The alternative I see is if you were going to try for a "rolling hills" effect:
The darker areas would still be very small compared to anything else...
Or they might be? a side effect of the texture.
I honestly find the texture to be the most distracting thing about the whole map, which is sad because I like your city layout. I think you have a great map here, but I think you could improve it a lot by getting rid of the "grass" texture, and expanding those cliff walls... or shading the ground by hand... something.
Anyway, that's my opinion, based on what I see. Then again, I see things differently than most people, so...
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