@Sigurd

Thanks, unfortunately I did draw every building by hand, using the pen tool in Flash CS3. As I mentioned, this took a lot of time, and is often not a necessary level of detail for most maps. One thing I learned, is that a lot city mapping is giving the illusion of detail, without the detail. Like clearly showing main ways, but hiding the details of alley way etc.

The shading and shadowing was done with filter styles in photoshop. Basically applying a harsh emboss and adding a drop shadow. Then I went through and individually colored building to mix up the shading.

RobA's link seems to be the direction I would take if I were to do it again. Make a pattern, twist it and rotate into appropriate angels, cut the streets, apply layer styles, and then go through and a the detail in areas you need it.