Earlier quoted context omitted.
Y’know what headphones really did “just work” though? Wired headphones, circa 2017. Their battery life was infinite. You could “pair” them in seconds to any device with a headphone jack, aka any device, because we’re in 2017. Oh, and they were cheaper and better for the environment. Courage, indeed. And this is why I’m currently typing my comment on an iPhone 6S...
I wouldn't let the lack of a headphone jack deter you from upgrading a phone if you wanted. You can get one of those adapter things and just leave it attached to your headphones if you wanted. I know people think it's annoying that you even have to do this but it's an option. I bet you can get one for free from a friend even. I do have a nostalgic feelings for the iPhone 4s and headphones. I wish there were products…
The problem is that I’d have to unplug that adapter to use my headphones with a device other than my phone, including other Apple devices like my Macbook. I would subsequently loose the adapter, guaranteed.
If the world could agree to use USB-C for everything, that might work, but Apple—who started this mess—is a prime holdout there.