Owning one of the newer MacBooks that were designed for bad typing experience, noisy fans and port(un)availability I was facing unusual challenges. Also due to the fact I fried one of my ports once before I became rather cautious about this device and using off-brand-adapters.
Having that challenge combined with the assumption, we would work on that project in a group setting and would need to collaborate, I followed a different approach from the beginning.
"The future is wireless"
Knowing there are indeed wireless-capable Arduino's and other microchips out there which would work straight out of the box with the IDE, it was even more tempting to achieve the same with a tethered Arduino. Of course calling solutions like this (or even wireless charging) "wireless" is doubtful as we are just creating another intermediary and moving the cable away from the laptop - but hey, it is not in my way anymore and I can start the hardware prototyping in a dedicated place without restraint.
Quick start - Ino 0.3 documentation
Warning! Inotool is deprecated and no longer maintained. But you can still install it - I personally still use it for the "serial" command I gotta explain later in this post.
sudo ino build && sudo ino upload && sudo ino serial