The design of green infrastructure in urban renewal sites is complex, requiring engagement with existing communities and future sustainable development goals, consideration of existing and future urban forms, changing climatic conditions, and the sites often being in low-lying and flood-prone areas. Traditional street tree decision-making approaches are inadequate for addressing the scale, environmental complexity, and mutability of decisions involved in urban renewal projects—new tree selection approaches that consider complex competing criteria for tree selections addressing stormwater management systems, visual assessment and solar amenity are needed. This paper describes a new method of multi-criteria street design decision modelling that combines outputs from hydrology modelling, digital procedural tree modelling and urban form analysis, with animation and gaming technologies. We evaluate our approach through application to the design of a large-scale, urban renewal project underway in Melbourne, Australia. The results of the study demonstrate the functionality of our model, which allowed the simultaneous output of streetscape visualisation, with tree selection responding to integrated stormwater management infrastructure and flooding, along with the likely overshadowing conditions of urban renewal built-form. Our multi-criteria approach makes a significant contribution to the tools available to urban designers, planners and landscape architects in their pursuit of smarter streetscape design decisions that respond to complex spatial, cultural and climatic urban challenges.