Years ago I had a similar experience flying out of Honolulu. 3 bags that I weighed the night before and all overweight on the uncalibrated airport scale. It was older lady who sternly told me I either had to shift the contents around to try and balance them out or pay over $200 between all the bags for the weight. She then spun on her heel and walked away. I stood there for a few seconds trying to decide my next move when a younger guy walked up, and just started ticketing my bags. He was way down at some other counter and had no idea what had just transpired. I nervously glanced to see where the old lady was and she was only 3 or so counters away but giving someone else the business, she never looked my way. The guy threw my luggage onto the belt and I bolted for TSA line and was practically standing on top of the person in front of me, fully convinced the old lady would come running to grab me out of line at any moment. Got through TSA onto my flight.
That happened with a friend traveling on JAL at JFK. It was also $100 charge. She was foolish enough to go into her bag to find $100. I told her open up the suitcase. We removed two laptops and some jeans. Voila! I saved her $100. The bag was accepted.
Not the same but this tip with dealing with customer service reps can be applied anywhere grocery stores, airports, department stores, etc.. Its best to choose a younger person who are not as militant about their job as an older Karen would be and you will be treated better and sometimes they let minor infractions slide!
I usually just wear a bunch of things and throw some other things out. My whole luggage put together probably doesn't have a hundred dollars of value in it 😂 (if I have expensive things they are on my person, either in pockets or a bum bag (in an emergency you can't bring bags, but I doubt they'd make you take of one you're wearing around your waist under your coat. The rule is so the luggage can't obstruct other people's path to safety by being dropped or taking time to be retrieved, so I assume a small bag that's secured around your waist for the duration of the whole trip would be exempt)