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Misconceptions on affordability remain a barrier to postsecondary access for millions of potential students. When students recognize financial aid availability during secondary school years, they gain the capability to better establish a curricular path that aligns with postsecondary aspirations. This dissertation assesses the use of residency-based financial aid programs and parents' college assets as methods to generate early information on postsecondary affordability. Following a three-paper format, the first paper develops a typology organizing the growing number of residency-based "Promise" programs around the country. The typology captures variations in the geographic scope for eligibility, supplementary qualifications, funding sources, value, and redeeming criteria to generate a description and list of comparable programs. Identifying program comparability is a necessary step for research examining program outcomes. The first paper uses a cluster analysis methodology to identify programs comparable based on the advertised operational characteristics. I find three distinctly different groups of residency-based financial aid programs, which I term state-based aid programs, institutionally funded programs, and community-sustained programs. The typology is extended to identify the specific operational characteristics for which residency-based, community-sustained financial aid programs differ. The second paper uses a unique institutional-level dataset and quasi-experimental Difference-in-Difference design to examine changes in college readiness, postsecondary outcomes, and curriculum decisions resulting from the residency-based, community-sustained Dell and Evelyn Carroll Scholarship. The award guarantees all Meridian High School students last-dollar funding for unmet need at Richland Community College. I find that information about Carroll Scholarship eligibility increases the college-readiness levels among high-achieving high school graduates who elect to enroll at Richland. After enrollment, all Carroll-eligible students register for, and earn, a statistically significant increased number of credit hours. I also find evidence that the Carroll Scholarship impacts student's curriculum selection. The final paper uses a quantitative, quasi-experimental design of the nationally representative Education Longitudinal Study of 2002. Propensity Score Matching models are used to estimate different parents' college asset savings strategies impacts the likelihood of a child enrolling in postsecondary education after completing high school. I find an enrollment association from parent's postsecondary savings across different socioeconomic and sociodemographic groups. The models evaluate student responsiveness differences based on socioeconomics, race, and ethnicity, and control for secondary school academic achievement and the amount saved. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]