The paper addresses the paradigm of adaptive reuse with a specific focus on issues related to the evaluation and the decision-making processes in this context. In more detail, this paper aims at recognising the main gaps that concern the evaluation process associated with adaptive reuse and providing some points of reflection and a preliminary methodological proposal to evaluate transformation scenarios related to adaptive reuse, through a multidimensional and multi-objective perspective. According to these purposes, this paper describes the implementation of the pillars of adaptive reuse to re-think the Corktown District of the city of Detroit, underlying through a real case study the complexity, the multidimensionality, and the multi-objective challenges of this concept, when implemented in urban planning and the revitalization of historic buildings. According to this scenario, the present paper focuses on issues related to managing the complexity and the multidimensionality of the decision process, under the analysis and evaluation of alternative adaptive-reuse strategies. This research, thus, proposes the application of the Multi-Criteria Analysis (MCA) technique, based on the Multi-Attribute Value Theory (MAVT), to evaluate and compare different strategic scenarios to re-think the Corktown District of the city of Detroit, according to the principles of adaptive reuse. The final result is a multidimensional evaluation that provides a final ranking of the different proposed alternatives, in order to support the decision-making to select the most suitable transformative scenario, according to the initial purposes of the project.