<p>This dissertation contains three chapters and focuses on the optimal design of fiscal policy and multi-item auction mechanisms where there is an informational friction in the economy. In the first chapter, I examine the optimal taxation of families in an environment in which (i) the earning abilities and child tastes of parents are private information, and (ii) child-rearing requires both parental time and goods. The optimal tax system combines an income tax schedule for childless families with tax credits for families with children. These components insure parents against low income and high taste for children draws respectively. The parental time and cost of goods involved in child-rearing have distinct impacts on the shape of optimal ...