Dates should update when itinerary is reorganized or dates on a previous waypoint are changed. For example, if I need to move something I planned to do on August 8 to August 9 instead, I would like all of my future waypoints should be pushed a day out, too. Maybe an option to opt into this behavior or confirm whether you want this to happen or not when you edit date. It could be frustrating for this to happen if you're just correcting a mistake or something that you don't want to impact the entire itinerary.