The insistence on having to install the xcode command line tools (hello "be at 99% installed for 10 hours" bug I have had over 5 different machines") is very annoyin. But I've found that brew has been a major mess as well.
Nothing like coming in on a Monday and having to debug 10 coworker's machines cuz suddenly python and postgres were silently upgraded (or some random shared lib was upgraded).
"Just use Docker" is also a PITA cuz of the abysmal file system performance stuff... I just want to run software! Or rather, I want my coworkers who might not be as well versed in system software to be able to have working systems.
All that being said, it's undeniable that I can daily drive Linux thanks to Mac stuff existing.