I gave up on this battle. I solved the problem by: 1) getting a good bluetooth DAC so I can use my high quality cans or IEMS and 2) keep a USB-C audio dongle around in case you forget to charge the DAC.

In the end I've come around to preferring this setup. Not being tethered to my device is, in the end, really pretty nice.

The current generation of iPad Pro doesn't have a headphone jack, and this iPad Air form factor looks nearly identical to the small iPad Pro. The writing has been on the wall for a long time. Headphone jacks are out!

I don't plan on moving to wireless headphonens for my iPad workflows, so it effectively just means an extra adapter I have to carry with my headphones.