By the 2050, it is estimated that the proportion of people over the age of 80 will have risen from 3.9% to 9.1% of population of Organisation for Economic Cooperation and Development countries. A large proportion of these people will need significant help to manage various chronic illnesses, including dementia, heart disease, diabetes, limited physical movement and many others. Current approaches typically focus on acute episodes of illness and are not well designed to provide adequately for daily living care support. In our rapidly ageing society, a critical need exists for effective, affordable, scalable and safe in-home and in-residential care solutions leveraging a range of current and emerging sensor, interaction and integration technologies. Key aims are to support the ageing to live longer in their own homes; make daily challenges associated with ageing less limiting through use of technology supports; better support carers – both professional and family – in providing monitoring, proactive intervention, and community connectedness; enable in-home and in-residential care organisations to scale their support services and better use their workforces; and ultimately provide better quality of life. Deakin University researchers have been investigating a range of emerging technologies and platforms to realise this vision, which we in broad terms coin Digital Enhanced Living, in the ageing space but also supporting those with anxiety and depression, sleep disorders, various chronic diseases, recovery from injury, and various predictive analytics. A Smart Home solution, carried out in conjunction with a local start-up, has produced and trialled a novel sensor, interaction, and AI-based technology. Virtual Reality (VR) solutions have been used to support carers in the set-up of dementia-friendly homes, in conjunction with Alzheimers Australia. Activity and nutrition solutions, including the use of conversational agents, have been used to build dialogue to engage and change behaviour. Predictive analytics, in conjunction with major hospitals, have been applied to large medical datasets to better support professionals making judgements around discharge outcomes. A set of lessons have been learned from the design, deployment and trialing of these diverse solutions and new development approaches have been crafted to address the challenges faced. In particular, we found that there is a need to consider user emotional expectations as first-class citizens and create methodologies that consider the user needs during the creation of the software solutions. We find that quality and emotional aspects have to be engineered into the solution, rather than added after a technical solution is deployed.