This dissertation consists of three chapters examining issues relevant to current higher education policy debates. In the first chapter, I use surveys, in-depth interviews, and administrative records from a sample of Wisconsin Pell Grant recipients who chose among Wisconsin public colleges and universities to explore whether students' initial college choices affected their early college experiences and to examine how this was associated with their persistence and achievement in college. After controlling for a robust set of observed characteristics, students attending their first choice college have similar levels of early academic and social integration into college life and similar academic outcomes when compared to students who did not attend their first choice college. In the second chapter, I use a form of cost-effectiveness analysis to estimate institutional performance and compare the results to popular college rankings, which generally reward colleges for attracting stronger students and spending more money. I use data from IPEDS, College InSight, and the Delta Cost Project for nearly 1,300 colleges and universities to estimate value-added to one important outcome: college graduation. I then adjust for two different types of costs for different audiences: the net price of attendance and per-student educational expenditures. All of the methods provide different results from the popular college rankings, suggesting that adjusting for costs and inputs yield a different set of high-performing institutions. In the third chapter, I address concerns about the timing of the current financial aid system, in which students from low-income families receive concrete information about the cost of college too late to academically and financially prepare for college. Using data from the Panel Study of Income Dynamics, I conduct a simulation of the effects of using a simplified eligibility process to make an early commitment of the full Pell Grant to eighth graders from needy families. The simulation of the estimated fiscal effects suggests that Pell program costs would grow by approximately $1.5 billion annually and the benefits would exceed the costs by approximately $600 million. [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.]