This paper reports early findings of a multi-city study of social wellbeing, neighborhood transformation, and the arts that builds on SIAP's Philadelphia research (Cultural Ecology, Neighborhood Vitality, and Social Wellbeing--A Philadelphia Project, Stern and Seifert, December 2013). The team used new data on Philadelphia to investigate ways in which two capabilities—economic wellbeing and social connection—influence four others—social stress, personal health, school effectiveness, and security. The appendix provides preliminary comparative data on four cities under study: Philadelphia, Austin, New York City, and Seattle. The paper was prepared for the Human Development and Capabilities Association September 2014 conference in Athens, Greece on the theme “Human Development in Times of Crisis: Renegotiating Social Justice.”