Creating a value proposition for an Information System (IS) is challenging: often consideration must be given to a broad set of users and range of individuals which may be directly or indirectly impacted by what can be both tangible and intangible factors. This becomes further complicated for large-scale deployments involving a number of disparate stakeholder groups and across multiple co-operating or competing organizations. Unfortunately, this is exactly the context within which many healthcare IS solutions must operate. A diverse set of arguments is being used by the different players variously seeking to design, develop, procure, implement and operate the IS solutions. This paper explores how the value proposition for IS in Healthcare can be created, providing examples of different approaches in use. It discusses the relative merits of four different approaches favoring one which appears to provide the most expedient and robust method - here termed `Pragmatic Modeling'.