Family caregivers (FCs) of children with medical complexity require specialized support to promote the safe management of new medical technologies (eg, gastrostomy tubes) during hospital-to-home transitions. With limited after-hours services available to families in home and community care, medical device complications that arise often lead to increased FC stress and unplanned emergency department (ED) visits. To improve FC experiences, enable safer patient discharge, and reduce after-hours ED visits, this study explores the feasibility of piloting a 24/7 virtual care service (Connected Care Live) with families to provide real-time support by clinicians expert in the use of pediatric home care technologies. This study aims to establish the economic, operational, and technical feasibility of piloting the expansion of an existing nurse-led after-hours virtual care service offered to home and community care providers to FCs of children with newly inserted medical devices after hospital discharge at Toronto's Hospital for Sick Children (SickKids). This exploratory study, conducted from October 2020 to August 2021, used mixed data sources to inform service expansion feasibility. Semistructured interviews were conducted with FCs, nurses, and hospital leadership to assess the risks, benefits, and technical and operational requirements for sustainable and cost-effective future service operations. Time and travel savings were estimated using ED visit data in SickKids' electronic medical records (Epic) with a chief complaint of "medical device problems," after-hours medical device inquiries from clinician emails and voicemails, and existing service operational data. A total of 30 stakeholders were interviewed and voiced the need for the proposed service. Safer and more timely management of medical device complications, improved caregiver and provider experiences, and strengthened partnerships were identified as expected benefits, while service demand, nursing practice, and privacy and security were identified as potential risks. A total of 47 inquiries were recorded over 2 weeks from March 26, 2021, to April 8, 2021, with 51% (24/47) assessed as manageable via service expansion. This study forecasted annual time and travel savings of 558 hours for SickKids and 904 hours and 22,740 km for families. Minimal technical and operational requirements were needed to support service expansion by leveraging an existing platform and clinical staff. Of the 212 ED visits related to "medical device problems" over 6 months from September 1, 2020, to February 28, 2021, enteral feeding tubes accounted for nearly two-thirds (n=137, 64.6%), with 41.6% (57/137) assessed as virtually manageable. Our findings indicate that it is feasible to pilot the expansion of Connected Care Live to FCs of children with newly inserted enteral feeding tubes. This nurse-led virtual caregiver service is a promising tool to promote safe hospital-to-home transitions, improve FC experiences, and reduce after-hours ED visits.