Abstract: Family caregivers of people living with dementia shoulder emotional and practical responsibilities, yet their own wellbeing often remains peripheral to dementia care. We built CareMirror, an envisioned caregiver wellbeing ecosystem with interconnected caregiver- and clinician-facing interfaces for longitudinal reflection, personalized support, and caregiver-controlled sharing with clinical care. We conducted semi-structured interviews with 14 caregivers, using CareMirror as a design probe to examine how they perceived this ecosystem and what expectations, concerns, and boundaries emerged around clinical connection. Caregivers valued attention to their wellbeing, longitudinal awareness, context-sensitive support, and clinical visibility when it could lead to meaningful follow-up. However, repeated reflection could become burdensome or emotionally difficult, automatic clinical sharing could inhibit candid disclosure, and participants wanted control over what information entered clinical care. They also expected AI to support reflection and communication without replacing caregiver voice or clinician judgment. We contribute design considerations for proactive, clinically connected caregiver wellbeing support.