Those rough shade sketches are just amazing! Honestly, I would play a game with those graphics! 
Anyway, I just did my first rough sketch, just to get an idea of what am aiming at... or trying to anyway. View point I think needs to be lower.
I intent to do the BG using 3D in Blender, but I do enjoy hand drawing once in a while, since it does help me visualizing up what my mind is seeing to what I want to show. Unfortunately, is very rare that I can actually draw what my mind sees... I~m better at drawing what my eyes see (or at least I used to be
).
Anyway, here for you to rip apart:

The Trader building is the "big" one in the middle, the tower I'm not sure, I just felt I needed something high on that side of the picture, to balance the scene... and once I put the stalls in the picture, I lost a bit of the walking area and "south exit".
EDIT 01 (10/06/2015, 00:05):
Original scan for sketch 1.
Original scan for sketch 2.

EDIT 02 (10/06/2015, 22:36):
Just posting my second 3D draft model. Am thinking this one works better than my 1st! (didn't post it, but if anyone wishes I can do that).
The Harbour Master's office building, still needs a lot of work, as the current shape looks odd - this happens when you have curves going of several opposite directions. I knew it would be tricky.
Still need to decide exactly where to add the opening with 3 steps to the lower docks level. Slicing the model to add it isn't much of a problem, but I can't later one just move it freely. Maybe some paint over the rendering picture will help, before I commit to it.

Currently unsure if I need to scale the buildings up and/or place them further away. Maybe I should just add a human model to the scene, just so I have some references. (yes, I know there's currently too much light and too little contrast. The top of the wall is blending into the path bellow, atm.)....

Anyway, I just did my first rough sketch, just to get an idea of what am aiming at... or trying to anyway. View point I think needs to be lower.
I intent to do the BG using 3D in Blender, but I do enjoy hand drawing once in a while, since it does help me visualizing up what my mind is seeing to what I want to show. Unfortunately, is very rare that I can actually draw what my mind sees... I~m better at drawing what my eyes see (or at least I used to be

Anyway, here for you to rip apart:

The Trader building is the "big" one in the middle, the tower I'm not sure, I just felt I needed something high on that side of the picture, to balance the scene... and once I put the stalls in the picture, I lost a bit of the walking area and "south exit".

EDIT 01 (10/06/2015, 00:05):
Original scan for sketch 1.
Original scan for sketch 2.

EDIT 02 (10/06/2015, 22:36):
Just posting my second 3D draft model. Am thinking this one works better than my 1st! (didn't post it, but if anyone wishes I can do that).
The Harbour Master's office building, still needs a lot of work, as the current shape looks odd - this happens when you have curves going of several opposite directions. I knew it would be tricky.
Still need to decide exactly where to add the opening with 3 steps to the lower docks level. Slicing the model to add it isn't much of a problem, but I can't later one just move it freely. Maybe some paint over the rendering picture will help, before I commit to it.


Currently unsure if I need to scale the buildings up and/or place them further away. Maybe I should just add a human model to the scene, just so I have some references. (yes, I know there's currently too much light and too little contrast. The top of the wall is blending into the path bellow, atm.)....