Family elderly caregiving is one of the preferred approaches for sustaining aging in place. While elderly people usually advocate for such an aging paradigm, supporting it represents an important challenge for family members, particularly in terms of coordination, resource allocation, and articulation of caregiving tasks. This paper presents Hermes, a digital assistant designed to help family caregiving stakeholders deal with the underlying challenges of such a process. Although the system is still at the prototype stage, its usability and perceived usefulness were evaluated with a sample of the target population. The obtained results are highly promising, showing that this challenge can effectively be addressed using technology, as well as generating a potential positive impact on informal family caregivers and older adults.