The area's fine - any mapper could legitimately choose to focus on the city 'proper' without environs.

Think about what you're portraying. If it is supposed to be a photorealistic aerial photo, that's one level of detail / realism. If it's admittedly a map somehow drawn to look like an aerial view, then some generalization / symbology / approximation is fine. If the latter, is it to be 'out of character', hence modern is ok, or is it somehow 'in character'? If in character, you have the problem that people with no actual aerial travel capability nor photographic capability wouldn't be expected to do a good aerial photo view - they just didn't think that way. Unless they were blessed with really high terrain nearby, I guess, to put them in the right mindset.

If you're doing the best you can to simulate a real aerial view, sameness is your enemy - all the roofs would hardly be the same color or construction... Unless you put in enough detail to suggest something like tiled roofs. I see a bit of bevel, which does visually lift the buildings into 3D... But are they all the same height? What kind of roofs ARE they?

If it's supposed to be somehow drawn or painted photorealistic, the walls, roads, docks, and water need some more subtle variation, and the texture needs to be smaller size. If those are *symbols* for those feature types, the level of uniformity and roughness are okay. Unless with the river you want to actually indicate depth/ current/ filth?

I like the 'towns grown together' effect, and the 'used to have walls' indication. It would be okay for the wall remnants to be even sketchier - castles and walls once no longer needed became easily mined sources of building stone. Having most of your buildings back from the shore seems good too - lots of folks forget the danger of tides and storms. Considering tides, it would be okay to show via shadows that the dock surfaces are somewhat elevated. And your admission of the lack of industry is apt - surely that many docking locations would at least call for a bunch of warehouses.

It's a great start, and even if you quit now it would be a decent product!