In 2010, the Urban Institute launched the one-year planning phase for the Housing Opportunities and Services Together (HOST) Demonstration, an effort to test two-generation strategies to improve the life chances of vulnerable youth and adults in public and subsidized housing. Over three years, housing authorities in Portland, Oregon, and Chicago, Illinois, adopted these strategies. At the end of the demonstration, Urban interviewed all the program staff to gather their reflections. This brief synthesizes these insights to provide practitioners guidance on what it takes to implement an effective, truly integrated two-generation model.