Follow-up studies of students with significant disabilities consistently indicate poor post-school outcomes. Although existing research indicates that services in inclusive general education contexts can result in positive short-term outcomes for these individuals during their school years, there are few investigations of the lives of adults with significant disabilities who experienced inclusive education over extended periods of time. Considering the lack of longitudinal studies, it currently is difficult to determine whether young adults lead more successful lives relative to employment, residential situations, use of leisure time, and friendships and social networks, as a function of inclusive education. This paper focuses on issues faced when conducting research to document the impact of contexts on long-term outcomes for students with significant disabilities, especially when addressing relative effectiveness of services in inclusive general education contexts and more restrictive contexts. Recommendations for future research and related policy and funding are suggested.