Family caregivers play a crucial part in assisting older adults as they transition into long-term care facilities, or Personal Care Homes (PCHs) as they are known in Manitoba. However, there is limited research on experiences family caregivers have with the health care system throughout this process. This study, through thematic analysis of secondary qualitative data, explored the experiences of 22 family caregivers as they transitioned an older adult across the continuum of care in Winnipeg, Manitoba. Particular attention was paid to the way in which caregivers were accorded choice and control within their interactions with the health care system. Caregiver experiences were juxtaposed with thematic and discourse analysis of secondary qualitative data including 9 service provider perspectives of navigating experiences, and public presentations of how the system is portrayed through governmental and regional health websites. The findings of this study are organized into three phases (pre-panel, panel, and post-placement) with associated sub-themes describing different aspects of structural burden throughout the transition process. Care responsibilities and requirements performed by family caregivers transcend typical assumptions of care provision, beyond social and medical care to often extensive and invisible administrative and information work. This thesis highlights the structural burden that accompanies providing care for older adults in the community, and in particular how this burden can further influence the need to initiate the transition process.