The present study extends prior research on additive and multiplicative ways by which family and neighborhood income relate to youths' well-being. Integrating substantive and methodological concepts, we demonstrate how various hypotheses would be revealed empirically with continuous income measures and clarify the relationship among different conceptual models. Substantively, we highlight ways in which match and mismatch between family and neighborhood income may encourage positive or negative social comparisons and may influence youths' ability to participate in social networks and to access enriching resources. We illustrate these models using a sample of 877 primarily white boys and girls representatively drawn from three US communities. We find that youths' receptive vocabulary is more strongly positively related to income in one context (family or neighborhood) when income is low in the other context (neighborhood or family), particularly for white children. Attention-deficit/hyperactivity disorder and impairment of daily functioning are highest among youth who live in contexts where their families' financial circumstances are advantaged or deprived in relation to their neighbors.