One of the key challenges in working in municipal government is making the proper technology choices and keeping one's technology current. This challenge is amplified in the GIS environment where technology change has accelerated recently. This paper will discuss such key issues as choosing between workstation and desktop environments, making the proper choice for a data editing environment, the emergence of client/server GIS, and the emergence of Web and Intranet GIS technologies. This presentation will cover the perspective of both new users making initial investments as well as mature installations that must face technology migration issues.