I'm hiring artist to draw a cartoon map of a residential neighborhood called "Maxwell Park" in Oakland, California
The style I'm looking for is this:
1) exaggerate the landmarks so they will jump out of the viewer.
2) only draw the important streets/highways, label their names
3) draw in prospective, show the horizon in the far end
4) it can be drawn by hand or digitally. Just mimic the style in the links above.
Audience: the people who live in the neighborhood. They are somewhat familiar with the landmarks.
Goal: the viewer will recognize "oh, this is my neighborhood" but glancing at the map.
Use: the image will be used on a 30-inch by 24-inch sign, taking up most of the sign space. Leaving only a small section for text.
Use google map, google earth, street-view, wikipedia, google image search and satellite images etc to help you understand the landmarks.
While you can exaggerate the size of the buildings, the buildings, the trees need to look carefully drawn (don't make it look like they are drawn by a children). It needs to look classy.