Housing shortages in the United States affect all persons but are especially impactful to low-income families who desire to move to high-opportunity neighborhoods. Housing is often seen as an intractable dilemma because of the emotional component involved with people wanting to preserve their neighborhoods as the same style to when they moved in. Scenario planning is an excellent tool for the modern planner at solving such intractable dilemmas. However, there is a gap in the literature regarding using scenario planning in smaller rural communities as opposed to regional scales or large cities. This does smaller areas a disservice as they could benefit from having tools to apply scenario planning methodology to the issues they face. The case study and proposed case study as part of this thesis work is to propose ideas for how scenario planning can be applied on a small scale to be replicated by other small communities. Both case studies were chosen to be relatively comparable in housing dilemma, one a very rural town in the Pioneer Valley, and the other being larger but facing similar conditions. The resulting methodology for housing enthusiasts to apply the methods in this paper to their own communities to replicate and have a productive conversation about housing.