Apart from the annoyance of the keyboard on the MBP and my personal preference for physical Fn keys over a touchbar, it is simply amazing to me how bad the Macbook Pro is with playing with simple external peripherals like Docks and external monitors. I've tried using a USB3 based dock, as well as a thunderbolt dock to connect 2 external displays to a Macbook Pro and it's just been horrible. The former didn't even work, the latter only supported one monitor for whatever reason. I then tried using 2 simply USB-C to HDMI adapters to connect to the two monitors (hello dongle land!) and while both monitors are seen, OSX refuses to support 1920x1200 on my new Dell 2415 Monitor and ends up stretching a lower resolution across the monitor, making everything look like garbage.
Occasionally, on reboots, it will work fine again, but it needs to be your lucky day. Why Apple won't make their own fucking dock so that I can pay them some extra Apple tax just for some sanity and peace of mind is beyond me. Meanwhile, my 2 year old Dell XPS (which I don't really love at all) has never had an issue with external monitors via any of these docks ever.
So here I am using WSL on Windows 10, and you know what, it keeps getting better and better, and I might just end up sticking around with Windows.