I don't know why the advisor was so pessimistic. I don't have any details about your secret projects or organizations to give me a sense of true service orientation. Impact, I think you have something, but in terms of being with someone not like you in alleviating distress, it is not clear from the description. Thus service orientation questions still come up for me, which could put your application on a lower priority for fit.
Indeed, mission fit is going to be important. Are you going to be able to let go of those VIP relationships and your organization to be the struggling med student? Are you willing to humble yourself and be the student and not the expert? Why would you leave something like that?