The international scientific debate on the growing concern over land consumption has gained prominence in recent years. The awareness of the link between cultural heritage and sustainable development has become increasingly evident, leading to a greater focus on the Adaptive Reuse (AR) of cultural assets as a conscious process of creating new values. This trend has prompted a reflection on urban planning practices and the promotion of AR and valorization policies for heritage, which can contribute to environmental sustainability, social cohesion, and cultural identity, thereby providing fertile ground for innovation and local economic development. However, decisions regarding AR interventions pose significant complexity due to the multiple interests at stake, as well as high costs that discourage investiments. For these reasons, this paper proposes a multi-methodological approach—applied to a project for the AR of a cluster of mountain huts located in the Sila National Park (SNP)—aimed at effectively supporting decisions related to the evaluation of feasibility and economic sustainability of cultural heritage landscapes that have not yet been adequately valorized. This approach was applied to a pilot project of AR, allowing for the discussion of the proposed evaluation methodological framework. The final step involved verifying the economic feasibility and financial sustainability of the methodology based on a Financial Feasibility Plan (FFP) of the proposed of the new destination to ‘Rifugio Diffuso’ (RD). The assessment aimed to evaluate the intervention’s ability to create value, generate a level of profitability that meets private investment expectations, and promote sustainable development of the local economy.