This chapter aims at developing critical perspectives on the role of quality of life in attractiveness discourses and policies of small and medium-sized towns (SMSTs). In changing contexts linked with the economic restructuring process, accurate effects of metropolization, but also a growing residential mobility of population linked with social demand for better amenities and quality of life, SMSTs’ local actors face challenges in the implementation of development policies. They are now confronted with different and sometimes ambivalent options: to develop productive and/or residential economies; to retain and attract businesses and/or people; to compete or cooperate with policy-makers in neighbouring towns; to reproduce successful models and/or try to promote innovative actions.