The current era is characterized by both unprecedented numbers and percentages of older adults in the United States and throughout the world, as well as glaring inequities in health and other resources among segments of the older adult population according to race/ethnicity and place of residence. Because it is important to understand the complex set of causal pathways and time delays that compound health inequities over the life course, we utilize a portfolio of systems science models that originated in the experiences of the community-based outreach program titled ElderSmile in northern Manhattan, New York City. This case study is intended to provide a behind-the-scenes account of our rationale for embarking on this program of scientific inquiry, the promise and pitfalls of a portfolio approach to systems science simulation, and our reflections on what is needed to better ensure that our findings may be used to advance programs and policies to promote health equity for older adults. Despite the time and resources required to ensure a participatory approach to group model building that elicits the knowledge of all team members across disciplines and fields of expertise, it is our belief that the simulation models devised may more accurately reflect real-world conditions and possibilities. If so, in the end, time and resources will have been well spent in the service of running virtual experiments that may effectively direct program enhancements and policy changes that improve the health and well-being of disadvantaged populations of older adults, not only locally, but globally.