City Mapping Technique

[Altrunchen]

For a long time now I have been wrestling with how to develop a repeatable, reliable, convincing, and aesthetically pleasing process for making city maps that are scaled to represent an area large enough to be a city. What I hope to accomplish is a method I can use repeatedly on all the cities in my campaign setting so that the players have a map to go to that isn't too memory-expensive but nevertheless looks nice.

What I have tried are the following:

Method 1.)
Basic city map with zoning instead of actual buildings to be populated with building images in MapTools:



Method 2.)
City map using pre-made images and texture templates to draw a city map in maptools

Method 3.)
Hand-Draw a city map and scan it into the computer for editing in photoshop.

Method 4.)
Hand-Draw a city map and scan it into the computer to be used as-is.

However, I never really like the results I get from any of these methods because the maps either look too sloppy, too under-developed, or are just too big to feasibly share online.

What I'd like to learn how to do is:

1. Develop a simple and repeatable system for drawing convincing and detailed city maps.
2. Develop a way to color-in said city-maps.
3. Make city maps that seem accurate to medieval city design.

Any idea how I can go about this?