This doctoral dissertation proposal is comprised of three separate chapters, all of which uses the nationally representative uniform survey Health and Retirement Survey (HRS) to examine the relationship between health, insurance, health care and health outcomes. Below, the brief introduction for each section is provided: Chapter I: Medicare Part D and Patients\u27 Well-being Chapter II: Parent\u27s Health Insurance and Informal Care Chapter III: Job Insecurity and Health (with Dr. Ayyagari) In chapter I, I explore how Medicare Part D (MD) affects the well-being of the severely sick patients both in the short- and in the long- term. I employ difference-in-difference (DD) alongside the instrumental variable (IV) model. The estimated result...