This paper considers why the decision may be made either to demolish or adapt existing buildings on brownfield sites and compares real-life decisions to those produced by theoretical design-support tools. Five case studies, including three individual buildings and two master plan sites of multiple buildings, were investigated through interviews with stakeholders. Reasons for retention included heritage value, architectural quality and government incentives, while reasons for demolition included maximising land value, lack of architectural significance and poor building condition. The analysis showed that the theoretical tools were useful for their intended purpose of analysing a portfolio of assets but that they could be improved by providing higher weightings for heritage values and extending the tools to assess different end uses and forms of adaptation. By testing the tools on master plan sites, the paper also identifies urban design variables, such as land efficiency, which would need to be incorporated for this purpose.