"Motivation: Docker for Mac was proving to be a workflow pain rather than a workflow gain."
I feel that pain. I switched from a Linux box to a Mac Mini for ALMOST all the work I do. I just couldn't take the pain, now when I need to do my Docker work, I just flip back to my Linux box. I have a Logi keyboard and Mouse with that 3 device button option, and a monitor with a few inputs, so I just turn on the ol' Linux box, press a few buttons, and I'm there. I do the same thing for Windows, for the rare occasion I need Windows (mostly for testing stuff).
I could probably find ways around the pain points, but I just can't be bothered when it's so easy to just use the other machine sitting right here. No point in wasting any more time on it.
Install Barrier on both Mac and Linux, get an extra monitor, and then you can seamlessly work on both system at once as if it's a single computer with multiple monitors. Don't even need to press that switch button on your keyboard and mouse.