This study presents a dynamic approach to collecting income information. We conducted a cross-sectional survey of 2,022 residents of historically underserved Appalachian Kentucky, an ideal location due to pervasive low income and our ability to control for potential confounders such as race/ethnicity and residential heterogeneity. In unadjusted analyses, nearly half of the sample indicated they struggled to meet their needs; 43% said they made just enough to get by; and 10% indicated they had more than they needed to live well. Adjusting for socio-demographic characteristics, proportionately more of those with lower self-rated health and a higher number of morbidities reported struggling to make ends meet. Less than 1% refused to respond to the question on self-perceived income sufficiency, compared with 20% who refused to report income levels. We conclude that self-perceived income sufficiency is a useful question to assess resources, both theoretically and practically, in an underserved population.