The construction of residential buildings in Italy has followed a cyclical trend depending on their location linked to both demographic and economic tendencies. The result is a building stock with heterogeneous characteristics in terms of age, building techniques, and materials. This heterogeneity, combined with the high fragility of the territory, necessitates specific analyses before planning building rehabilitation interventions, whether structural, energy-related, or functional. This requires time and economic resources, and does not allow for effective planning at urban scale. This research explores the possibility of creating a process that can evaluate building rehabilitation interventions qualitatively and on a large scale. Two groups of buildings constructed with public funds in the municipality of Bologna in the period following World War II are compared. The analysis was conducted using a database compiled by the research group as part of an ongoing study. It includes 468 building records and 211 attributes covering general data, construction characteristics, spatial organization, energy performance, structural integrity, and building functionality. Through specific queries, the parameters of buildings designed and constructed by private individuals (group PR) were compared with buildings designed by public agencies (group PU). The study highlights the main differences and similarities emerging from the analysis of the sample of constructions with regard to various aspects: (1) distributive; (2) technical; (3) energy-related; (4) structural; and (5) formal. The results obtained, and the expected performance derived in qualitative terms for each building, made it possible to formulate initial considerations in terms of the applicability of large-scale building interventions.