Gesture-informed patient management systems and related medical devices and operating methods are provided. A method of assisting operation of a medical device using a sensing arrangement capable of detecting physical movement by a user involves detecting a configuration procedure performed by the user in response to output of the sensing arrangement indicative of one or more gestures with respect to the medical device by the user, determining a current state of the user within the configuration procedure based at least in part on the one or more gestures with respect to the medical device relative to a sequence of gestures corresponding to a defined sequence of tasks for the configuration procedure, and providing a graphical user interface display on a client device comprising guidance information influenced by the current state within the configuration procedure.