Drats... that looks like it should do the job without any issue at all

Right, in a nutshell, this is the best way to do some debug stuff. We need to replace the config/safe mode firmware in this case, as you don't have anything else on that Oak yet, so only the config/safe mode firmware is running.
For that,
you'll want this... it's the Arduino sketch that the Oak runs in safe mode. Put that in a folder called OakSystem, and you'll be able to compile it on the Arduino IDE. But before you do that, you'll need to go and edit a line one of the board core files. On windows 10, this is located in %appdata%\..\Local\Arduino15\packages\digistump\hardware\oak\1.0.6\cores\oak\OakParticle. Not sure on mac, linux it would most likely be (~\.Arduino15\packages\digistump\hardware\oak\1.0.6\cores\oak\OakParticle). In that folder, you are after a file called particle_globals.h, where you'll remove the comment ('//') from in front of '//#define DEBUG_SETUP' on line four. That's it. Compile the OakSystem.ino, and then load it onto the Oak using the Arduino IDE board type set as Tools -> Boards -> Oak and Tools -> Upload Using -> Serial (Expert Use Only).
You may want to also have a look
at this wiki article before you begin... walks you the process of doing a serial upload to the Oak, and the setup stuff.

Hopefully you can make sense of all of that, and will get some more sense out of what's going on. Let me know if I goofed up on something or something still doesn't make sense...