As the “baby boomer” portion of the U.S. population ages, the need for different types of living communities increases. At the HealthSec 2024 workshop we first presented the personal experience of the first author who lives in a continuing care retirement community, identifying technology opportunities for three healthcare challenges: (1) Signs-of-Life, (2) Signs-of-Health, and (3) human asset management. This paper extends this previous work with the feedback we received at the HealthSec 2024 workshop. While we discuss technology solutions ranging from no technology up to artificial intelligence, along with these technology solutions are corresponding security and privacy risks. We feel it is important to raise these healthcare challenges in order to focus attention, stimulate research investment, and encourage innovation for senior living environments. Going forward, we suggest researchers seek the involvement of residents in geriatric living environments to serve as “participant observers” helping to determine the appropriate technology solutions and risk management tradeoffs to address the unique healthcare challenges presented by the demographics of our aging population. We would also encourage researchers from other countries with different senior care health systems and social cultures to join us in what to this point has been a U.S. centric study effort.