I've only ever had to provide date and city pair, but I agree that the repetition is annoying. A few weeks ago, I used the text system because I did a SDC and wasn't appearing on the upgrade list for my new flight. Got the automated "Thanks for being Platinum" message, and then immediately after "Are you a Medallion Member?" "What's your tier?"
The automated system is entirely useless, but in most cases I've found the agents to be good.