Homelessness is on the rise around our nation, with the COVID-19 pandemic exacerbating the problem, and homeless families with children struggle to become self-sufficient through securing and maintaining stable housing and adequate employment. Local organizations are seeking ways to identify and meet those areas of need while making efficient and effective use of their resources. In Brevard County, Florida, Family Promise of Brevard (FPB) has implemented a transitional housing model in its stabilization program to provide support and services to families seeking to break thecycle of homelessness and achieve self-sufficiency. To determine the program’s effectiveness, an analysis of secondary data gathered from families who have transitioned to stable housing will determine if the length of time a family spends in the program affects their level of self-sufficiency in terms of stable housing and financial independence. Control variables of race and ethnicity of head of household, gender, age, number of people in the family unit, and the type of household structure are used to determine if they influence program effectiveness and family outcomes. While the results indicate that demographic variables have a limited impact on self-sufficiency over time, the two significant indicators of self-sufficiency through the Stabilization program are housing and employment. Additionally, the results indicate that the families who stay longer in the program are more likely to be the individuals/families who need more services and assistance to achieve self-sufficiency. Along with the secondary data analysis, a qualitative interview data with a family in the program was analyzed and it shows that relationship-building and life skills are important aspects of the program and FPB staff make a difference through their time, compassion, and dedication spent assisting families in breaking the cycle of homelessness.