Why have the greater number of blacks not been able to get and stay ahead? How have some, despite the unfavorable odds, been able to climb? What might we learn from the experience of this second group? These questions matter for our understanding of intergenerational and intra-generational thriving in the rural and urban contexts. In their totality, these and related questions enumerated throughout this work, invite an intentional focus on whether there have been and now are patterns to the routes, rates, and stability of movement toward the middle and upper class over two generations.