We use Geo Blue annual family plan for medical. We also have a NetJet membership for medical evacuation/repatriation just in case we don't like what Geo Blue considers suitable evacuation.
Chase Sapphire coverage for trip cancellation/interruptions is $20K per trip if purchased on Chase. Pre-existing conditions exclusions apply. We usually, not always, self-insure for cancellation/interruption above that.
We always book cruises with Sapphire to get the double points.