Based on the observation that care pathway organization in France is complex and asymmetrical between stakeholders as pluri-professional caregivers (medical staff, nurses, etc.) and care receivers (patients, family helpers), we tried to replace that specific French organizational context in an acceptance projection of multi-user interactions through the technology itself. By interviewing fourteen French participants during six months respectively at work or at home - depending on each user profile, among both patients and caregivers, we deeply examine their perception of what kind of more collaborative information technology (IT) features could be helpful. Thus, our research intends to analyze what key functionalities appear as more significantly collaborative compared to others and doing so, trying to find a better understanding, classification, and measurement of multi-user interaction in healthcare services using innovative technology. Focusing on the study of multi-user interaction impacting technology acceptance, we find new perspectives for prototyping such collaborative tool in e-health services to better fit and predict technology acceptability in this medical context which, to some extends, highlights contradictory requirement needs for multi-users.