The “City Induction” research project aims to develop an urban design framework at the scale of site planning consisting of three modules: formulation, generation and evaluation. This paper presents the start of the on-going research on the evaluation module with the aim of identifying and discussing the assumptions behind its development. The evaluation module will be driven by sustainable urban development principles, which determine the design analysis criteria and benchmarks, and it will be structured around selected urban analysis and design methodologies. We discuss the challenges of bringing these two domains together, and propose to incorporate techniques of interaction and video game design towards a more meaningful and inspirational design experience.