This dissertation answers three questions in urban and labor economics. Chapter 1 investigates under what conditions wealthy, high-skilled landowners wind up worse off when they use housing regulations to make their communities harder for poorer, low-skill workers to move into. If there is labor complementarity in production between high-skill and low-skill workers, low-skill workers will have lower productivity when they cannot advantage themselves of neighborhood effects, which in turn will hurt high-skill workers. Chapter 2 asks whether rent control, a strong form of housing regulations, incentivizes landlords to evict their tenants when the unregulated rents rise. Exploiting a known price shock to different residential buildings throughout San Francisco over an 11 year period, I find that a 2\% increase in prices leads to a 1\% increase in the monthly probability of an eviction from a controlled unit. The analysis also highlights the perverse incentives created by rent control, that medium-term (3-5 year) market withdrawals increase when prices increase. Chapter 3 studies whether grandchildren change their grandparents' labor force participation, and then researches whether the fall and rise in labor force participation between 1970 and 2009 can be ascribed to the rise and fall in grandparenthood due largely to the Baby Boom. I find that being a grandparent lowers labor force attachment for both grandfathers and grandmothers on both the intensive and extensive margin, but that grandchildren play only a limited role in the trends in older men's labor force participation.