The modern educational landscape is in rising need to reflect real-world work life also in university-based learning environments. New models such as learning factories and project-based or challenge-based learning foster practical skill development and move beyond theoretical knowledge by using hands-on practical skills or by including challenges from the industry directly into lectures. Although the university provides a learning factory in the field of production technology, the authors of this paper will focus on practical learning settings outside the university campus, at the sites of real companies. This study provides an analysis of project-based learning methods implemented at Deggendorf Institute of Technology (DIT). We compare five learning formats: the “Digitalization College,” the “Healthcare Challenge,” “Project Based Learning”, “Real Projects”, and a healthcare-related winter school at the campus at location Bad Kötzting. All formats include real-world challenges from the public or private sector and employ collaborative learning models where student teams must divide tasks and present group solutions in interdisciplinary and sometimes even international teams. The “Digitalization College” is thematically open and focuses on interdisciplinary collaboration with a time horizon of two semesters and the final goal of developing prototypes. The “HealthCare Challenge” is an intensive, short-term training course focusing on rapid problem-solving in rural healthcare. “Project Based Learning” is a one semester-long teaching program focusing on entrepreneurship and AI, while the main goal of “Real Projects” is to foster entrepreneurship and deep collaboration with respective companies. The health-care related winter school at Campus Bad Kötzting tackles public health care- related topics in an intensive week of international and interdisciplinary learning and working. Using interviews and course evaluations, the analysis shows that while all trainings offer real work life learning experiences, each format presents distinct benefits and challenges, depending on their learning context, structure, and objectives. The structured nature of “Project Based Learning” is well-suited to specialized knowledge improvement, whereas the flexibility and real-world engagement of the other three trainings emphasize entrepreneurial skill development and interdisciplinary work.