The Italian public real estate counts many historic buildings, commonly underused or degraded. In the Campania Region more than 1,900 structures built before 1980 have a recognised cultural value. Moreover, in the aftermath of the COVID-19 crisis, a renovated interest in the field of healthcare services, architectural heritage and climate change has emerged. In this scenario there is the opportunity for the structural and technological enhancement of obsolete but valuable healthcare architectures which goes along with urban and social regeneration. The aim of this study is to provide tools which can support public authorities defining and monitoring interventions to better manage their architectural heritage. To this purpose, a list of indicators has been developed to assess constructive and typological characteristics of existing buildings to evaluate their propensity to be recovered and reused. Relevant examples of monumental hospitals which need renovation are placed in the city of Naples. These infrastructures, really important for social and cultural reasons, have been selected as case studies to test the feasibility of the indicators. The results show that the transformability of historic buildings is heavily linked to structural and typological characteristics. When comparing buildings with the same structural system, the presence of architectural and constructive limitations as well as the spatial distribution become critical.