Mass loss is important for our understanding of the late evolutionary phases of massive stars, including the formation of Wolf-Rayet (WR) stars and determining what type of supernovae various systems will become. However, small changes in mass loss rates cause very different theoretical predictions for the evolutionary path and supernovae end state for a massive star. For example, massive star winds are expected to be clumped, but this lowers overall mass loss rate estimates to a point where theoretical models cannot explain the observed number of WR stars. Additionally, massive binaries further complicate the mass loss picture because they lose material and interact with their local environments in several ways that single stars cannot: through mass streams, accretion, and mass loss via outflows in Roche-lobe overflow systems; and through stellar winds in colliding-wind systems. In this talk I will focus on presenting results from studies of a small number of systems that provide an in depth look at the circumstellar structures that can form during periods of heavy mass loss. In particular, I will show data from many observing techniques and wavelength regimes that, when viewed all together, present a three dimensional view of where circumstellar material is located in massive systems.