Hi folks!

I'm planning a game of DnD for some friends. I'm an absolute rookie when it comes to designing towns, cities, lands and whatnot. Although I must admit, there's something about it that has always intrigued me, which is why I've decided to do a somewhat ambitious (for me) map of the largest city in the known world.

In the scenario, the town is ruled by a twilight silver dragon. Twilight is the first time in a dragons life where its force is actually diminished with age, and this particular dragon is quite weak, though ancient and wise. It resides inside and beneath the Sky District, in the mountain.

I'd like to force-feed you more about the story, but I'll stick to what's relevant for the design choices.
The city is designed in a manner that's supposed to aid defense. The upper right road leads to the main gate and the easiest way to transport large masses of soldiers to and from the center of town. Because of that, this road is lead alongside the mountain housing the Sky District. From there, defenders will be able to severely decimate enemy forces, until they have reached the natural entrance up to the mountain. From there, they will face the kingsguard.

The city is focused on trade, so there are already quite a few zones serving that particular purpose, and more to come.
The silver dragon is suffering from atmospheric dissipation (forgot the fantasy-correct term atm) and is slowly diffusing into the very mountain it lives in. As a result, increasingly large veins of silver has been enriched into the mountain during the last 500 years. It is one of the major sources of the citys wealth, but fool is he who thinks the city would succumb to invasion were it not for this. Under the dragons ruling hand, the city has prospered both politically and socially.

The ruler is kind-hearted, which is why the city have only a relatively small pool of low-class citizen, instead housing a substiantial amount of middle class houses and citizens.
The thieves guild have taken root in the low class district, they are a tough group to keep out. The district is supposed to have only one entrance/exit, but the numerous tunnels in the old city district, which was built before the dragon laid claim to the town, makes moving in and out of the low class district a breeze...Provided you have the knowledge and connections.

These (among other) districts and buildings can be found right now:
Storage, warehouses and granaries.
Guild halls.
Red light district.
Middle Class
Lower Class
Slum / Deadtown
Religious / Divine

And these districts/buildings have yet to be added:
Library / Educational
Royal / Noble
High Class
Military (kind of covered in the major military district to the immediate left of the town square, but I was thinking a distint military building of sorts. More of a mental note)

Before I did more sketching, I was curious to what the experts on the topic have to say?
Does it look cluttered? (Might be hard to tell at the moment, smaller roads and individual buildings will be added in the next stage)
Does it "flow"? If you came by boat as a tradesman from the south, would it feel natural to dock, unload cargo and move about the city?
Anything that strikes you as particularly odd/out of place/out of scale?
Click image for larger version. 

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