Homebrew barely works. I dread messing with it. It's not Homebrew's fault: with Macs the stars have to align to get things to work much of the time. I find that the origin OS for most of my libraries (Linux/Debian) is much more reliable than a Mac. I had some issues switching away from a mac at first, but I got over them.
Brew works great most of the times and it is indeed very human friendly. The problem sometimes arises when you need to install something a little bit more exotic than usual (eg. graph-tool was my last case) in that case lot of things can go wrong.
Yeah as long as you're using what everyone else is using and stay "inside the lines" it's OK. But step off into special territory, you're better off on Linux.
Brew recently started refusing to install anything if your xcode is out of date, and forces you to wait for a "brew update" if it hasn't updated in 24 hours. It's actually hideously user-unfriendly, but it probably saves the devs a lot of stupid github issues.
It's working for me but I would love to have an example of breakage to take to my IT as another reason they should allow the company machines to be updated.
The only time I remember having a problem with Homebrew is in the summer where I'll run some beta version of the new macOS on a testing machine while trying to use Homebrew which does not support the beta.
Other than that it never fails for me, and I install a boat load of tools through Homebrew. I even install as much of my GUI tools as possible using brew cask.
Homebrew is a "package manager" that has worse dependency management than a ham sandwich and a community that reacts to criticism with "don't talk to us, you're being negative".
