The southern Piedmont of the southeastern United States epitomizes the complex and seemingly intractable problems and hard decisions that result from uncontrolled urban and suburban sprawl. Here we consider three recurrent themes in complicated problems involving complex systems: (1) scale dependencies and cross-scale, often nonlinear relationships; (2) resilience, in particular the potential for complex systems to move to alternate stable states with decreased ecological and/or economic value; and (3) uncertainty in the ability to understand and predict outcomes, perhaps particularly those that occur as a result of human impacts. We consider these issues in the context of landscape-level decision making, using as an example water resources and lotic systems in the Piedmont region of the southeastern United States.