As a classical musician with a slightly-too-long-but-fits-just-fine instrument, my annoyance is that the only metric is size, and not suitability for checking. I guarantee 99% of overhead luggage is stuff that can be checked just fine and musical instruments simply cannot be, but for some reason this isn’t allowed to be a consideration.
I get panic attacks every time they look like they are going to get persnicketty about carryons, because I’ve had some confrontations over it and even had to buy an extra ticket on the spot once (long story, but I certainly rejoiced when that airline ceased to be). Just a couple days ago a delay caused me to miss my connection on Southwest and I just about flipped out on the agent because I’d paid early bird check in and on the new flight instead of the A group I was at the end of the Bs. The randomness of never knowing when you’re going to get fucked with is what makes it so stressful.