The interpretation of multi-spacecraft heliospheric observations and three-dimensional reconstruction of structured and evolving solar wind is challenging. This is especially true for the interpretation of white-light structures observed by the Heliospheric Imagers (HI) onboard STEREO spacecraft since their appearance depends on three-dimensional geometric factors. Numerical simulations can provide global context and suggest what may and may not be observed. We use the heliospheric code ENLIL to simulate various scenarios of well-defined corotating solar wind streams and ejected transient density structures, and we generate from the solutions synthetic white-light images at various locations. We illustrate that corotating interaction regions (CIRs) show up differently in HI-2A and HI-2B and that they may appear as transient structures in HI-2A but not in HI-2B. This asymmetry is caused by differing Thomson scattering responses. Further, we illustrate that a given interplanetary coronal mass ejection (ICME) may exhibit drastically different white-light brightness depending on the observing position and that some ICMEs can eventually reach Earth without being detected by the imagers. Finally, we demonstrate application of the modeling system through simulation of the 24 – 25 January 2007, 31 December 2007 and 26 April 2008 CMEs.