I use a `brew bundle` to help manage this. Make a `Brewfile` listing homebrew installs, then `brew bundle cleanup` to delete everything that's not in that file. This way I can try something out and easily delete it (and the dependencies it installed). It also obviously makes it easy to setup a new machine.

This has been my MO with home brew as well. But it’s not perfect. Unix-style apps don’t always behave nicely when it comes to cleanup and it’s easy to get borked, not to mention the difficulties that the homebrew folks go through each time there’s a new release of Mac OS. I really think the writing is on the wall and we’d all be better off dumping homebrew and just using VMs.

You can use Homebrew and MacPorts concurrently. I will always choose the MacPorts version of a tool given the option and only fall back to a Homebrew version when absolutely have no other choice. It's frustrating to have to use two tools but I've found it easier to keep my dev environment clean this way.

Wait; do you mind sharing a bit more about how you do this? I somehow missed this reply, and appreciate the pointer

I haven't had to do anything fancy yet. I just install both and try to find the MacPorts equivalent first before using Homebrew.

For example, I use the MacPorts version of Python. If I need any Python dependencies I install them either via MacPorts or pip.

In fact, I only have two Homebrew packages installed: dockutil and mas. Both are tools I use as part of ansible scripts which don't have MacPorts equivalents. All the remaining Homebrew packages are all cask apps (Firefox, Chrome, Discord, Slack, etc.). Those don't have any dependencies that would cause any conflicts.

For comparison, I have 139 MacPorts packages installed. 2 Homebrew packages, and 21 Homebrew cask apps.