I eventually landed on pipx as fighting with Pyenv and Anaconda - via Miniconda - was an exercise in frustration. There's some mucking about in `$HOME/.local`, but this is mostly self-contained and not a huge chore to keep running.

Coming from the Homebrew/Ruby ecosystem - Hey @mikemcquaid - installing a entirely separate package manager just to deal with a few projects felt like the wrong thing to do.

Occasionally, I have still needed to compile Python myself in order to get things to work, which isn't guaranteed not to blow up w/ `brew`, but this has become far less common of late.