Quote Originally Posted by Larb
It's an interesting city but I think the overall texture is a bit harsh. It makes the outline of the guild district buildings harder to make out. Maybe made a bit subtler so it doesn't dominate the image so much. Also I think your land/hill contours might have a bit too much white in them. Might be worth changing it to light brown instead.
I approached this first with an oil painting filter, which made the rivers look quite nice, but overall detrimented the texture. I applied a basic Gaussian blur: 1px radii. For now, I removed the contours, and will approach them again when I'm going through finishing. Thank you!

Quote Originally Posted by Sushipopsicle
The annual battles make me assume that the city would slowly divide itself with inner walls
I tried this, and I think it will help me "solidify" (maybe not the right word) workflow of the buildings.

Here's the NEARLY COMPLETE first district: Uptown. Also new walls.
 

The new array of central walls protect an area called the Bullseye, a central nexus for trade and communications. (Also the location of possibly Aboleth mind-control devices, hoards, and various merriment.)

Now, I've marked out the specific districts:
 

Yellow is Uptown: A district defined by the Lone Man's Theatre and it's prime land-importance. It is also the holding ground against ground assaults.
Navy Blue is the Guilds District: A conglomerate of crafting and financial interests, most likely controlled by scheming entrepreneurs and filled with opportunities for buying ships, airships, and/or funding the downfall of the city.
Pink is Cliffside: An aristocratic riverfront array of properties - hidden lust, blood feuds, and plenty of hor d'ouerves.
Purple is the Lord's Land: Land dedicated to Bowyer Castle and the Riverwatch Citadel - power centers of the fief and city.
Green is Bull's Center: Centered around the Bullseye, along with the Cathedral of Saint Baptise.
Red is the Slums: Perhaps when the mind-control is lifted, a religious revolutionary emerges in the dirty back alleys of the city.
Teal is the Docks: Maybe a cult of necromancers was paying off the sailors a pretty penny to keep up shipments of the tainted waters - once it's gone, they'll be looking for skulls to crack!

Thoughts on the entire worldbuilding aspect and implementation are much appreciated, and thank you all for your input so far!