Governments and development stakeholders pay great attention to issues surrounding international migration because they are of great concern not only to destination countries but also transit and countries of origin. Strategic issues relative to international migration are human loss, insecurity, migrant smuggling, kidnapping, criminal networks, health, integration and border management among others. Noteworthy is the lack of consensus on management approaches and consequences of international migration among stakeholders, particularly migrant sending and receiving countries. There is, however, a measure of agreement that international migrants have the capacity to contribute to development of poor countries and West Africa comes to focus in this instance. Two perspectives exist relative to diaspora’s/international migrants’ contribution to development: the celebratory perspective and the pessimistic perspective. This chapter, therefore, examines the profile of diaspora investments, challenges and coping mechanisms of the diaspora relative to investments and the influence of the diaspora’s investments on development through a Nigerian case study. This chapter is within the intellectual and pragmatic frameworks of intersectionalities of international migration, the diaspora and development in West Africa. Data for this chapter was gathered in Nigeria from 2019 to 2020. The findings suggest that the diaspora engages in many different investments for various reasons but not without nearly prohibitive challenges. They have, however, innovated strategic coping mechanisms with creative contributions to development through investments within critical checkered experiences needing multi-level attention from states and non-state actors for sustainability.