This study investigates how varying the analytical emphasis placed on political and security-related indicators shapes citizen satisfaction at the regional level in Romania and the Republic of Moldova. In a socio-political environment characterized by institutional transformation and evolving security challenges, identifying the combined and separate effects of these dimensions is critical for designing effective regional policies. The empirical analysis employs a grey clustering methodology to classify counties into three distinct satisfaction categories. To capture the sensitivity of outcomes to indicator prioritization, five predefined analytical configurations are constructed, reflecting different emphases on political versus security factors. The results show that under political-dominant configurations (100% or 80%), a larger share of Romanian counties (22–24 out of 42) are classified in the highest satisfaction cluster, while Moldovan counties are predominantly located in the lowest cluster. Conversely, under security-dominant configurations (80% or 100%), between 23 and 28 Moldovan counties are assigned to the highest satisfaction cluster, whereas 36–37 Romanian counties shift to the lowest cluster. These consistent structural shifts across predefined analytical configurations highlight the context-dependent role of governance and security perceptions in shaping regional satisfaction patterns.