Many health information technology (HIT) researchers and practitioners strive to improve healthcare systems by creating and using engaging and effective technology. However, the challenges researchers face while conducting research in the healthcare context are rarely discussed; HCI researchers who come from non-health-related backgrounds and conduct research with populations with highly complex health scenarios (e.g., chronic conditions, severe/multiple disabilities) encounter situations they are not prepared for. Researchers often handle those situations by adapting various methods ``on the fly.'' Those ad-hoc methods are often unreported in the literature, which can perpetuate the cycle of being unaware of these challenges and leaving future researchers unprepared. This paper presents our experiences during three of our works-in-progress research projects; we report the challenges we encountered and the methods we adapted while working with populations with complex healthcare needs. Finally, we propose preparation guidelines for future researchers and call on the HIT research community to engage in more dialogue about implementing a standard approach to engaging with such populations.