This paper reports on the study of best practices in evaluation methodologies for aging in place technologies, and analyses their feasibility in a pandemic environment. The pandemic situation, with various physical distancing restrictions in place, especially for vulnerable older adults, has increased the importance of deploying health monitoring and social interaction technologies for aging in place. The pandemic also made it more difficult for researchers and developers of technologies to evaluate the usability of home health monitoring technologies. Existing technology evaluation methods mostly involve laboratory and home technology usability evaluations that could be problematic during physical distancing restrictions, and are not well suited for rapid evaluation of health monitoring technologies. The increasing trend in virtual doctor and health professional visits puts additional pressure to speed up innovation for home health and wellness monitoring and communication technologies without increasing risks for vulnerable populations. Researchers observed challenges with performing HCI research with older adults in a pandemic situation, including challenges with participant recruitment, obtaining informed consent for the study, shipping technology to the willing participants, assessing the ability of older adults to set up both digital health technology and remote usability tools, and research data collection. The need for low cost, low risk, easy to use and privacy-preserving usability evaluation methods and tools for home health monitoring is growing rapidly, and new remote usability evaluation methods and tools will add to the growing arsenal of digital technologies used in the public health response to COVID-19 and beyond.