Have you tried using the Determinate Systems installer? This (supposedly) helps to not break everything on system updates. As far as I can tell, it works.

My biggest issues with homebrew were dealing with versions of dependencies. If major updates for a package came out and you ran a `brew upgrade` (or a new member joins the team and installs it for the first time), it often wasn't trivial to switch back to the old version. Or if two projects have conflicting dependencies, for example one project was updated for imagemagick 7 but another still needed 6, that was an absolute nightmare to manage when using homebrew.

With nix, each project can define its own dependencies that have no impact on other projects. Combined with direnv, all you need is to `cd` into your project and you have the all of the dependencies at the right versions in your PATH.

Additionally, while definitely more complicated, nix (with nix-darwin and home-manager) can do way more than homebrew does. You can declaratively define pretty much the entire configuration for your machine.

I got a new Mac last week and with just a `git clone` and a few commands I had all my CLI tools installed, dotfiles setup, desktop apps installed, and even all of my macOS system settings configured.

I'm recently back on macOS for work, and I wanted to love nix-darwin, but just couldn't get it even installed / basics running well enough to start to enjoy configuring things with it. The whole flakes mess really doesn't help.

(Maybe if you're already running NixOS and familiar with the latest it's a lot easier.)

I couldn't even uninstall it cleanly, since the Mac was new I gave up after some time and decided it was easier to reinstall macOS (which takes several hours but at least I can just leave it and then know that it's done).

So I'm back to (purely) brew (and scripts to `defaults write` etc.).

My frustration with brew is that it's getting increasingly opinionated, and those opinions are not familiar to me from any other OS/package manager... Like if you want postgres v15 you have to `brew install postgresql@15`, and then even if that's your only installed version it's 'keg-only', which means it's not on your PATH, and their suggestion is to dump some stuff at the end of your ~/.zshrc, which aside from the fact you're not using zsh and they could tell that, just seems dumb.

Then there's python & npm packages... They're deprecated and being removed as independent formulae, so don't do it like that. You're not allowed to install them with the python/node formula you installed, so don't do that. So what do you do, `python -m venv ~/system-python-venv` or something, activate it, and install in there. And now remember to activate that every time you want to use a command that happens to be a python package so you had to install it there. Or dump it in the end of your zshrc, I guess!

I have used brew trouble free for many years.

I stuck with home-manager standalone for many years, but after setting up other nixos configs I found myself wanting to 1) align systems more closely and 2) manage more system-level stuff on darwin. It took some time to rework my standalone modules to nix-darwin modules but overall I'm really happy with the result.

I run everything through an idempotent 'rebuild' script, so I don't really notice any day-to-day difference between nixos, standalone HM, or nix-darwin.

With or without flakes works nearly identically if it is just home-manager configurations

I use it to install a bunch of Homebrew casks and a small number of regular packages to support those casks. It works perfectly well!

My biggest annoyance is that Homebrew is really slow; the Homebrew part of my Nix-Darwin rebuilds usuay takes 3-5x as long as everything else combined. Homebrew is really slow even when it has nothing to do.

The only caveat worth mentioning is that the module built into Nix-Darwin doesn't support installing Homebrew itself. Instead you tell it the prefix for an existing Homebrew installation.

(There is an out-of-tree module for installing Homebrew as well, but I haven't tried it.)

Extremely well, even supports passing arguments (`--HEAD`) through and integrates with services for casks too, so it can restart things like postgresql when homebrew updates it.

Having nix-darwin uninstall brews not declared in the flake makes me stay honest about keeping my configuration up to date as well, if I've just `brew install x` to try something it'll get removed next time I apply my config. Needs adding to the flake to keep it installed persistently, which in turn means my config tends to be up to date.

I prefer to keep most of my homebrew stuff (especially casks) in a nix-managed Brewfile with some logic about when to run/update.

That's a great setup for package management. Stuff like Nix-Darwin and Home Manager start to shine when you want to also do some configuration management. For just package management, your approach is probably better in that it's simpler.

The language itself isn't as challenging as the overall structure of NixOS/nixpkgs itself. It's a monolithic source-tree of interdependent "derivations". The entire notion of "package" has been thrown halfway out the window. There is logic and reason to the madness, but it's really difficult to find your bearings.

So the barrier to nix is... nix? No, the language is not the problem. It is not a particularly difficult language at all. There are plenty of actual problems to address, but the language isn't the issue.