This dissertation consists of two chapters. First, I explore the role health dynamics play in determining the value and cost-effectiveness of public health insurance. Current healthcare consumption may yield future health benefits that lower longer-run expenditures. I leverage exogenous variation in the expansion of Medicaid under the Affordable Care Act to assess how comprehensive insurance affects immediate healthcare spending for the near-elderly (aged 60-64) and future healthcare spending once they receive Medicare at age 65. I provide evidence that Medicaid coverage increases immediate expenditures by roughly 112 percent; but, after receiving Medicare, the same individuals are healthier and consume 77 percent less care measured by total expenditures. I then develop and estimate a life-cycle model of near-elderly individuals that incorporates the Medicaid expansions as well as dynamic health investment and endogenous mortality. I find that the Medicaid expansions were valued by the near-elderly population at slightly above net government costs, and that modest reforms to increase Medicare's generosity could generate considerable welfare improvements relative to program costs. Second, I document that flexible employment and educational arrangements can reduce the barriers that some students face in seeking a degree by mitigating the contemporaneous earnings losses associated with enrolling in college. Using detailed data, I analyze how labor supply and study efforts respond to changes in labor market conditions and college activities/tasks. My findings indicate a low ``short run" opportunity cost of studying when working. I also show that study time is not particularly sensitive to changes in labor market conditions. Consistent with these results, I find that workers take advantage of their flexible schedules by changing their usual working hours when their college courses are more demanding. Encouragingly, I do not find adverse effects of work hours on academic performance or of study hours on workplace performance. Finally, students value flexible working and educational formats highly and view online education as an important vehicle for increasing expected future income. Overall, this study underscores that combining flexible working and learning formats constitutes a suitable path for many students who work to pay for college or workers who aim to improve their skills.