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 over wifi! It even usually works!"
Uhm, no, you're just supposed to spend the $19 on a USB C -> Lightning cable to connect them.
The wifi thing is just convenient for many people. If it's not good enough or "pro enough" for you, there is still a cable that you can use.
I don't really see the problem here. Assuming I buy the base model MacBook Pro and the cheapest iPhone 8, I've just spent $2000 dollars and I don't see how I can justify complaining that I need to spend an extra 1% on a cable to connect them.
It's not a workaround, it's an additional capability.
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.
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 over wifi! It even usually works!"