I think I started using homebrew some 4+ years ago. I have no idea what a cask, tap, pour, or whatever is. At first things "just worked" and it was great.
Then came the couple of afternoons where I had an important project to finish, and I had to upgrade X. I think once it was matplotlib (for which I had to upgrade pip? ... I can't remember) or something silly like that. Everything broke, I had to reinstall all my python packages (that's when I moved to pyenv), and I did not finish my work on time. There was probably an easier way, but I was (am) a newb and I didn't know how.
I remember brew was one of the first command line utilities I ever used and thought, "woah, that was easy _and_ cool!", but I no longer think I am the target audience.
Someone might say the onus is on me to learn more about the tools I use, and they are probably right. I need to know my .tmux.conf or .zshrc or whatever to get the most out of those, too, and sometimes I like to dive in. For the most part, I just want to Get On With My Work and be oblivious.
If you could provide some guidance, I would genuinely be grateful. For a newbie like myself, when I see comments like "just set HOMEBREW_NO_AUTO_UPDATE=1" and then back and forth on why that does and doesn't work, I decide I don't have time for this today and cross my fingers I don't need to brew install anything in the near future. And if I do, I will probably avoid it (because it will take, I don't know, hours?).
However! You shouldn't be using your system package manager to install Python dependencies! As you know, since you moved to pyenv. But I don't think it's fair to blame homebrew for getting you into trouble when doing that; one also wouldn't use apt to manage python packages.
In fact if you look at this thread, many supposed problems with homebrew seem to be in fact problems with python package management. It's the same with all languages isn't it -- ruby and rbenv and gem, node and nvm and npm, rust and cargo. As soon as you start actually installing 3rd-party dependencies, you're better off using something language-specific to install the interpreter / compiler / toolchain, better than using homebrew or apt etc.
Macports is a tougher sell for an average user today simply because the disparity in popularity means macports library is smaller and older. But macports is engineered more correctly.
This was my biggest complaint about Homebrew. Does it mean it was finally fixed?