Here is a recent illustration of Pike Place Market for Visit Seattle with the excellent art direction by Joe Paul (Visit Seattle). These map Illo's are challenging. Below is my process from sketch to final. I fall into the trap of trying to be accurate to the actual layout of the buildings and streets and it makes me stiffen up. I should of added more stuff to it make it filled with more activity. At least try it and see if it works. The informational aspect makes me more conservative.