This document describes the evolution of a GIS map application for the City and County of Honolulu. It started as basic maps on the city's website and has expanded to include more advanced functionality. Recent upgrades include moving to ArcGIS Server 10 and new hardware. New features have been added to the map like showing nearest parks, routing directions, and printing maps. Developing the application requires balancing the needs of different city departments and stakeholders while working within a limited budget. Simplicity and usability are important to make the tool accessible to non-experts. Testing with different user groups can help achieve this.