MacOS a coin toss and Linux being robust regarding drivers/hardware support on desktop? Are you talking about Hackintosh, or do we not live on the same planet?
What phone are you having issues with? Every android phone I’ve used will communicate with adb. iPhone has never used USB mass storage, and support for that has nothing to do with MacOS.
Can’t comment on the daisy chain issue, I just learned that was a thing.
Screen will remain black. Or, screen will power on, display nothing. Or, screen will power on, mouse cursor will appear, but no password prompt.
No such problem with Linux.
Yeah there are things Linux doesn't support but just don't buy them. The things that it does support generally don't require any driver installation.