Research-based design has been foundational for landscape architecture. Analytical layering in geographically-based mappings has become a universally applied, formulaic approach. For waste landscapes, this has generated similar redevelopment strategies for drastically differing waste landscape conditions. This site typology, however, requires more nuanced approaches. As a design-research framework, “landscape lifecycles” aims to tackle waste landscapes with integrative strategies and techniques that reactivate waste as a legible and dynamic contributor to local and regional contexts; a method for integrating multiple diverse programs rooted in economic, environmental, and social performance to form hybrid assemblages in the transformation of perceived material and spatial waste. This article highlights design-research and generative representational methods developed through projects and coursework that embrace speculation as a means of engaging with waste conditions at multiple scales — from the material to the region. These methods range from speculative geographic, process, and abstract mapping to scenario testing to time-based, projective design that document, explore, and test an argumentative hypothesis and the multi-scalar design implications of research on the imaginative potentials of waste transformation.