Distributed Software Development involves a number of different business models, and companies intending to embark on the journey of distributed development have difficulty choosing the model(s) that suits their process and current software practice. More literature that presents similarities as well as differences among these models, in terms of processes, practices and challenges that characterize them, is thus becoming critical to software practitioners. This paper intends to bring more knowledge in this direction. We present empirical evidence from a case study of DSD practice in five companies that had projects following one or more of the different DSD business models described in the literature. We discuss the similarities and differences in the challenges faced by the projects in these models, as well as the relationship between the models, development process, and project size and complexity, as reported in the projects studied.