AI and Deep Learning have led to the development of many tools for healthcare and medicine: image-based diagnostic tools, note-taking aids automatically transcribing speech, medical risk assessment and decision-support applications based on the patient parameters stored within Electronic Health Record (EHR) systems. The astonishing success of Large Language Model-based generative AI has further demonstrated a great potential for employing AI-based tools in many domains of human activity, including healthcare and public health. At this point, the majority of AI applications in healthcare are tools that work autonomously, and the physicians and medical personnel are called to use them as an input in their decision making outside of their use of EHR systems. We discuss the opportunities and challenges of employing AI-based capabilities within EHRs and outline a research roadmap for creating interactive collaborative integrated EHR assistant applications. We discuss parallels with our prior work in addressing usability of enterprise resource planning systems.