This dissertation investigates the complex connections among loan debt burden, student experiences, and post-bachelor's outcomes, situated within the framework of systemic disparities in educational funding and opportunities. It identifies declines in state funding across educational levels as a systemic and politicized issue, disproportionately affecting students in underserved and underresourced school districts. The study emphasizes the impact of systemic racism and policymaking in perpetuating poverty through higher education, emphasizing the need for equitable policy establishment. Economic downturns and reduced higher education funding necessitate the exploration of alternative revenue streams, such as endowed funds and fundraising efforts, to prevent increased tuition costs that may limit accessibility. Navigating higher education poses challenges for students accumulating significant loan debt, impacting their life trajectories. Underserved students face unique barriers to education, including increased family responsibilities and the need to work, often multiple jobs. The critical quantitative study, utilizing a structural equation model, reveals associations between gender, race, dependents, and various life outcomes, emphasizing the influence of these factors on loan debt stress, federal loan debt, stop-outs, working hours, and loan borrowing. Notably, higher cumulative loan debt is linked to post-bachelor's stress, employment impacts, and delays in major life events. The research emphasizes the pressing need for policy interventions to address systemic disparities, ensuring equitable access to education and promoting positive post-bachelor's outcomes including financial viability, livelihoods, and well-being for all students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]