Help needed: Need to find 'good' tutorial and tips for Cityscape map

[Sapprine]

So, Im Quinten, 18 year old man from the Netherlands and I've trapped myself in a little bottleneck situation here.

You see, ive been playing Warcraft III since I got it for my 8th birthday (over 10 years ago). Im a master at recreating 'vanilla (blizzard)' terrains.
I know how to replicate that enviorment you feel when playing through the original campaign chapters like no other men.

I wish I could say that for every tileset, though...

I really suck at Underground, Dungeon and Cityscape maps, but have found creative ways to 'dodge' them. (Using Lordaeron Winter, Outland or Northrend for cave maps).

But recently, I got a request by proud hive user @Pyraeus to redesign the city of Stratholme for what we like to call 'The Grand Reign of Chaos Overhaul' (expected release date in 2 or 3 years)

I'm currently on my 2nd attempt, the first one was OK, but a bit of a mess...
(little use of cliffs, linear roads and paths and all houses were in boxes)

I'd like to start over, but I just suck too damn much at the tileset...

Are there any good tutorials on how to make a thriving, recourceful, urban Cityscape map?

 

[lord_Turin]

try looking at realistic city design, or medieval city design for that matter.
there are clear quarters, poor, rich, tavern, markets, barracks, middle class, industrial areas etc.
if you start with adding such designated areas to your city it will surely come alive more.