In the last decades, the territorial planning shift toward the topic of regeneration, together with the awareness about built heritage’s key role for sustainable development, has led to greater attention to built heritage reuse as a conscious process of new value production. However, decision-making regarding the reuse of built heritage presents significant complexity, as it involves striking a balance between preserving the material and intangible values associated with heritage assets and ensuring the long-term sustainability of their intended functions. This complexity has historically deterred both public and private investments in reuse interventions, resulting in the gradual abandonment of these significant cultural artifacts. Considering these challenges, there is an urgent need to complement the cultural discourse surrounding heritage reuse with its economic implications. Accordingly, this research investigates the factors that enable or hinder the financial sustainability of projects focused on reusing built heritage. To achieve this objective, the study provides a theoretical overview of heritage reuse and discusses its practical implications. Subsequently, it proposes a methodological approach to investigate the financial viability of six projects aimed at reusing various heritage assets in Italy. This comparative analysis identifies common factors contributing to the success or failure of these projects in achieving long-term sustainability. Moreover, the research pays particular attention to understanding how different management models may influence the feasibility of reusing a specific built heritage asset. By examining various case studies under different management scenarios, the research seeks to provide insights into the complexities of decision-making surrounding heritage reuse and offer recommendations for enhancing the economic viability of such endeavors.