Absolutely no disagreement with the core principle that what matters is the listening experience. That is a given!
Where you and I will disagree is that it sounds like you are saying measurement will not matter in predicting if the gear will always fare well across the board. Modern gear like amps and DACs CAN exceed the limits of human hearing, and often do so handily at consumer friendly-ish prices. But I don’t think all modern gear does. Again, to state the simple and obvious example of an amp with high output impedance... you will detect a difference compared to low output impedance amps when listening to low impedance headphones (exception probably being planers) and IEMs.
If faced with equally good sounding gear, offering roughly the same features, and costing roughly the same, you would not go wrong choosing the better engineered (as measured) offering. But, again, I will agree, it has to sound good to you. I just want to make sure it will always sound good as the situation changes and new headphones and IEMs are introduced into the mix someone listens to.
To again agree with your core principle, I would not bother upgrading soundly engineered (any deficiencies are beyond human hearing) gear that sounds good to you. But, if your amps and DACs sound good now, but are poorly engineered, they might not sound as good when you change your headphones. If you are at your end game on headphones and IEMs and like how they sound, well yeah, that’s audio - and wallet - heaven!