This study empirically investigated the structural relationship between household life-cycle stages and housing market conditions in shaping owner-occupied housing choices. Using repeated cross-sectional data from the 2010 housing recession and the 2020 housing boom, three analytical approaches were employed: cross-sectional comparison within the same time point, comparisons of identical life-cycle stages across varying time points, and life-cycle transition analysis. Results revealed that during the recession, the likelihood of homeownership declined after the stabilization stage, whereas during the boom, it continued to increase through the contraction stage. Notably, comparing identical life cycle cohorts across different time points indicates a structural shift in determinants—from a focus on “permanent income and user cost” to “net assets relative to income.” Furthermore, the life-cycle transition analysis confirms that decision-making structures within the same cohort were reorganized in response to changing housing market conditions. In conclusion, homeownership choice emerges from a complex interplay between micro-level household characteristics and macro-level market dynamics, highlighting the need for adaptive housing policies responsive to evolving market environments.