This dissertation examines how family processes reproduce inequality across families and generations in the context of broader structural transformations, including rising inequality, changes in mothers’ labor market positions, and fertility decline. Together, the three chapters analyze how these large-scale shifts reshape the mechanisms through which socioeconomic and gender inequalities are reproduced within households and across generations.The first chapter investigates how parental financial investments in children are an important pathway for the intergenerational transmission of socioeconomic status. Using data from the Consumer Expenditure Survey (1990-2024), this study examines how the relationship between married couples’ educational pairing and spending on children has evolved over time. I find that the gap in parental spending across family types has widened substantially over the past decade. In particular, families in which both parents hold a bachelor’s degree have increasingly outspent other family types, net of individual mothers’ and fathers’ education and household income level. Juhn-Murphy-Pierce decomposition results indicate that this growing gap is driven less by differences in income levels and more by differences in how families translate income into child-related expenditures. Over time, college-educated homogamous families have become more likely to allocate a larger share of their resources to children, amplifying disparities in parental investment. These findings suggest that the consolidation of educational advantage within families has intensified its role in reproducing socioeconomic inequality across generations. The second chapter examines whether parental occupational gender composition is associated with children’s occupational gender-composition trajectories from early adulthood to mid-career. Using the Panel Study of Income Dynamics, 1968–2023, I identify distinct trajectories of occupational women’s representation between ages 18 and 44 and assess whether these trajectories are linked to the gender composition of mothers’ and fathers’ occupations during childhood. The analysis identifies four trajectories: persistently low women’s representation, rising women’s representation, declining women’s representation, and high women’s representation. Trajectory membership is strongly patterned by child gender. Beyond these gender differences, fathers’ occupational women’s representation is associated with sons’ trajectory membership: sons whose fathers worked in occupations with higher women’s representation are less likely to remain in persistently male-concentrated trajectories and more likely to follow trajectories involving movement across the occupational gender-composition distribution. Mothers’ occupational gender composition is not consistently associated with children’s trajectories, and there is little evidence that these associations vary by childhood paternal coresidence. These findings show that parental occupational gender composition is linked to children’s longer-term patterns of stability and movement across gendered occupational locations. The third chapter examines how fertility decline reshapes local institutional conditions for family life by focusing on childcare availability in South Korea. Using administrative data on all registered childcare centers from 2016 to 2022, I examine neighborhood-level trends in the ratio of available childcare slots to the number of age-eligible children. I find that the average number of slots per child increased, although the number of childcare centers declined during this period. This pattern coincides with a faster decline in the child population than in the number of childcare centers. However, the distribution of childcare availability became more polarized. While the overall average increased, both zero-availability and oversupply neighborhoods became more common. Differences in childcare availability by neighborhood poverty also narrowed or even reversed, as tracts in high-poverty counties experienced greater increases in slots per child than those in low-poverty counties. These findings indicate that fertility decline is accompanied by a complex reconfiguration of spatial inequality in childcare availability, reflecting a temporary equalization alongside emerging signs of polarization. Together, these chapters show that structural change reshapes not only the distribution of resources, but also the mechanisms through which inequality is reproduced. The dissertation therefore highlights how changing configurations of family advantage, gender, and demographic context shape the reproduction of inequality across generations.