Qualitative analysis is an important part of design education for Human-Computer Interaction (HCI) students, teaching interpretive skills such as empathy, observation, and contextual understanding vital for designing human-centered solutions that address user and community needs. Unfortunately, there are few opportunities for students to learn qualitative analysis in an experiential, real-world setting where students engage deeply and rigorously in discussing and evolving themes iteratively. This is particularly difficult in the context of the increasingly large class sizes typical of HCI education today within large public universities. In this paper, we share lessons from the design of a course module and supporting platform aimed at organizing a class of over 120 students to learn qualitative analysis while contributing to a collaborative needs assessment project for a local non-profit. We describe the design choices made and findings from semi-structured interviews on challenges students face and aspects of our design that helped to mitigate those challenges. We found that students can struggle with motivation and with understanding of ideal practice when engaging in a rigorous qualitative analysis process. However, these can be mitigated through engaging with real-world clients and stories, structuring the course for collaboration and coaching, and reducing cognitive and information processing burdens. Experiencing the process end-to-end, and not stretched out over too long of a period, was important since understanding and appreciation for earlier steps often came in later stages. We conclude with implications for the design of course structures and digital tools for expanding real-world experiential learning in computing and HCI education.