The prevalence of chronic diseases and the recent global spread of deadly communicable diseases such as Covid-19 has resulted in changing global health needs that require new and adaptable approaches toward delivering healthcare. Healthcare digitization has aided in dealing with old and new healthcare issues, and there is still enormous untapped power. This power can further transform healthcare delivery systems provided that safe and accurate aggregation of individual health data is achieved. We explore a typical patient's healthcare pathway for two major chronic conditions, namely 1) cardiovascular and 2) mental diseases. The aim is to reveal healthcare delivery approach changes as used in the past, present, and with a look to the future to manage these diseases. Furthermore, we provide a holistic overview of the technologies behind the digital healthcare transformation. The study also offers a roadmap that depicts the evolution in the healthcare delivery system enabled by these technological health advancements and concludes with a critical evaluation of such systems.