Building on the rich tapestry of demographic and economic research, this paper extends the analysis of the Second Demographic Transition (SDT) within the milieu of Czechia, Slovakia, Poland, Romania, and Austria, shedding light on the nuanced interplay between economic variables and demographic indices such as the Total Fertility Rate and the Sobotka’s Second Demographic Transition Behavioral Index (SDT1). Drawing from an extensive dataset spanning over two decades, the study applies Pearson’s correlation analysis, Holt’s Exponential Smoothing, and stepwise regression to unravel the complexities of demographic behaviors in the face of economic prosperity and inequality, as measured by GDP, Gini coefficient, and the Human Development Index. The findings reaffirm the pivotal role of economic factors in shaping demographic trends and highlight the divergent paths Czechia, Slovakia, Poland, and Romania have embarked upon compared to Austria, a representation of Western Europe’s demographic evolution. This comparative analysis underscores the significance of wealth distribution in influencing demographic outcomes, offering a comprehensive understanding of the second demographic progression in the context of economic transitions. The research contributes to the broader discourse on demographic changes, providing insightful implications for policy and future studies in the dynamic landscape of Central and Eastern Europe and beyond.