Earlier quoted context omitted.
Have you tried the WiFi running/debugging? Works pretty well for me.
This is seriously where we're supposed to be for a pro laptop? It shouldn't work "pretty well" when you're using a $2000+ machine. It should work perfectly every single time. This is what built apple into the company it is. "pretty well" wasn't good enough. This sounds like the type of concession I would have made in 2005 on my gentoo laptop. "Yeah, USB doesn't work, but there is a workaround that sends that data ove…
Before they added this feature, a USB cable was the only way to do this, and it still works, and works reliably. If you have a USB-A connector on your Lightning cable, you'll need an adapter, if you have a USB-C connector, you won't.
From the OP's complaint, he didn't like having to do this with USB, so I suggested the WiFi option to avoid cables. Maybe you read that as "the USB option does not work", which is not the case.
WiFi depends on the quality of your WiFi network. Mine is rock solid, so "pretty well" is my engineer answer to cover the cases when AP is flakey, range is crap, etc.