Couple of thoughts.
Customer service in general is somewhere between poor and terrible. No excuses for Princess, but wondering why you would bother dealing with Princess on the phone as there are lots of great TAs out there that will handle the garbage for you. One web site with help you by having TAs Compete for your Cruise business.
The other is if you get an agent that clearly needs training . . Three steps. #1 Say thank you, goodbye #2 Hang up #3 Call and get another agent.
As for medallions - why are you wasting time trying to order? Faster topick up at the port. For 3 cruises total added time under 5 minutes. Bet you wasted more time trying to order
As for dining - if you cruise us after September 14th you need to wait till June 17th. Again, unless you need to eat at 6pm, go directly on boarding and organize. Lots easier than needing to link your reservations. A group is almost impossible on the app. Maybe worse on the phone. Easy on board.