This paper explores subjective poverty as complementary to traditional income-based measures. Drawing on original data from the MYPEOPLE project—a survey conducted across three Italian regions (Lombardia, Toscana, and Campania)—the study examines how regional and household characteristics shape self-reported economic and social vulnerability. We constructed two indicators of subjective vulnerability: the first assesses difficulty managing essential expenses, and the second captures limitations in maintaining a social life. Using a hurdle negative binomial model, the study evaluates both the probability and intensity of vulnerability. Results reveal significant territorial and family-type disparities. As for the first indicator, households in Campania report higher vulnerability levels. Single-person households and lone parents show a greater risk of experiencing at least one hardship. At the same time, they share the greater intensity of vulnerability, once affected, with couples with children. Concerning the second indicator, households in Campania face higher odds of vulnerability, though intensity levels are similar among regions. Lone parents with children are the most at risk of experiencing at least one deprivation, though intensity differences among household types are non-significant. These findings highlight how perceived hardship—shaped by geographic and familial contexts—offers critical insights for designing more targeted, context-sensitive social policies.