My issue with this is that the CS rep reframed what is essentially theft--assuming it's a straight up error on Apple's part--to the tune of hundreds of dollars as "frustrating," and then suggesting that oh yeah, "it's frustrating to me too".
This is handling on the part of the rep, and it's not "frustrating," it's infuriating.
To take the example to the extreme, imagine if you get a call from a cop who tells you that your child has been killed, and they say "I know it's terrible, but it's terrible for me too, I had to call you about your dead kid."
Even if it's broadly accurate that it is "frustrating", the CS rep will go home that night not short a few hundred dollars because a giant multinational corporation just... took it.