Designing technology-mediated connections between patients, relatives and healthcare providers is a main focus of electronic healthcare (eHealth). Involving future users in the innovation and design of eHealth is important for understanding the complex socio-technical challenge of connecting key actors in health management. This paper presents the results of a research project on the design of eHealth solutions for hearing healthcare. We introduce a client journey perspective on hearing rehabilitation and present how we engaged elderly hearing aid users, relatives and healthcare providers in inventing future eHealth-assisted client journeys. Our analysis of this problem space presents a series of boundaries and barriers and possible bridges and connections for future hearing rehabilitation. We synthesise these results by developing an integrated model of the complex interplay between information, communication and learning among key actors in hearing rehabilitation and we outline four implications for design within this framework.