The answer is: all the way. I don't understand any other conclusion you could draw from this. Other than a few non-essential command line tools (like emacs), Apple will clean the system of anything they can't control.
A lot of code is shared between OS X and iOS, so the 'tivoisation' clause means that they can't use GPLv3 on iOS, so best to avoid it on Mac OS X too.
Homebrew will still be around to install all the command-line goodies you need. No pain in the ass required.
Regardless of Apple's goals in this action, a lot of the OSS world is moving to permissive licenses, so this isn't a terribly surprising move.