Clearly, the goal of a soul stuck in complacency life after life after life, would be to break out of that routine somehow, some way. Is this one of the greatest challenges there is for Creator, higher selves, and other divine stakeholders in attempting to coax an incarnate individual back onto the path of divine alignment? Without divine healing requested by incarnate humans, how successful are these attempts in general?

This is certainly a major obstacle in attempting to help humanity. Because they have the gifts of free agency and free will, they must be allowed to have their choices and live with the consequences. We can encourage, we can remind people of other possibilities at times, and sometimes entice them to make a better choice when they are at a crossroads, particularly when there is prelife planning to take a certain direction at key turning points in their life, but we cannot force things on humans ever, we can only bring up possibilities and encourage the humans to embrace them. So as you can imagine, and as is reflected in your question, this is an imperfect and uncertain system at best, because humans vary widely in their openness to change, and their acceptance of more positive and uplifting pursuits that might not be in keeping with a dark path they may have embarked upon. Going back towards the light can be more difficult with such a departure. This is what happened to the spirit meddlers who turned away from love and light and could not find a way back, and at this time, cannot even conceive of doing so having been cut off entirely from divine support. So, much is at stake always with how a person conducts their life, but they have the last word, they are in charge and in control of their own existence while incarnated as a physical human. We cannot override their decisions, we can maneuver things around them to bring solutions their way, to bring positive influences in the form of information or other people who might be a mentor and do an outreach to possibly save them from a difficult series of choices in a life that will lead to failure, but there must be something from within them still able to connect to the higher self, and be open to accepting its suggestions and encouragement to move in a positive direction, for anything to change them for the better. This can be a long and frustrating road. We know all humans can be saved and find a path back to the light, but it does not always happen within a given lifetime. Sometimes a series of lifetimes is required for them to ever reach a more successful life journey that makes gains and accomplishes some healing of the past trauma and loss of capability. Those old problems and wounds must be resolved and repaired, otherwise the Law of Karma will bring the same discord, negativity, and challenges to them over and over again, even in new lifetimes, as a stimulus to reconciling things they put out of alignment through poor choices in the past, as a way of re-establishing a balance to their part of the universe.