In recent years, we have seen an influx in reliance on AI assistants for information seeking. Given this widespread use and the known challenges AI poses for Black users, recent efforts have emerged to identify key considerations needed to provide meaningful support. One notable effort is the development of ChatBlackGPT, a culturally informed AI assistant designed to provide culturally relevant responses. Despite the existence of ChatBlackGPT, there is no research on when and how Black communities might engage with culturally informed AI assistants and the distinctions between engagement with general purpose tools like ChatGPT. To fill this gap, we propose a research agenda grounded in results from a preliminary comparative analysis of outputs provided by ChatGPT and ChatBlackGPT for travel-related inquiries. Our efforts thus far emphasize the need to consider Black communities' values, perceptions, and experiences when designing AI assistants that acknowledge the Black lived experience.