Regarding cable integrity. Am I the only person to have had headphones pop in my ears due to (un)plugging the cable or causing some kind of friction at the connector?

I assume that issue disappears with the new plug.

Oh, and your complaint about charging the phone while listening, that's the Apple way they've always removed options to have a cleaner design. The superior Apple solution is to buy their pricey iPhone dock with headphone jack hidden in the back and charge and listen at the same time. Not a fanboy, just adding that Apple has addressed your complaint by making more money off of you ;)

It wasn't even the point of my post, but I'll bite: a digital cable means you no longer have to rely on the form factor/budget constrained DAC included in the device itself and can go for DACs of your own choice. That doesn't necessarily imply improved audio quality, but it means you have more control over your audio quality.

A digital cable can also do error handling and correction, meaning damage to the cable does not have the same impact as it does on analog cables.

Yeah, you only have one port. But that's not a restriction of digital ports but of Apple's implementation, I fully expect Android phones with two or more USB Type C ports to be released. As you can see from my post I'm not a fan of Apple's implementation at all (despite the fact that it'd be merely a nuisance for me).