Homelessness is a primary concern for community health. Scientific literature on homelessness is wide ranging and diverse. One opportunity to add to existing literature is the development and testing of affordable, easily implemented methods for measuring the impact of homeless on the healthcare system. Such methodological approaches rely on the strengths in a multidisciplinary approach, including providers, both healthcare and homeless services and applied clinical researchers. This paper is a proof of concept for a methodology which is easily adaptable nationwide, given the mandated implementation of homeless management information systems in the United States and other countries; medical billing systems by hospitals; and research methods of researchers. Adaptation is independent of geographic region, budget restraints, specific agency skill sets, and many other factors that impact the application of a consistent methodological science based approach to assess and address homelessness. We conducted a secondary data analysis merging data from homeless utilization and hospital case based data. These data detailed care utilization among homeless persons in a small, Appalachian city in the United States. In our sample of 269 persons who received at least one hospital based service and one homeless service between July 1, 2012 and June 30, 2013, the total billed costs were $5,979,463 with 10 people costing more than one-third ($1,957,469) of the total. Those persons were primarily men, living in an emergency shelter, with pre-existing disabling conditions. We theorize that targeted services, including Housing First, would be an effective intervention. This is proposed in a future study.