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Should I set up this project with conda, miniconda, virtualenv, docker, some combination of the above...? Fuck it, I'll just use R.

You can install R and some commonly used R packages with:

conda install r-essentials

Homebrew installing Python and installing virtualenv and virtualenvwrapper makes life easy.

All of these methods people are listing that requiring me to do more than manage one file (requirements.txt) is sort of missing the point.

I get that a lot of Node developers are coming to Python to do things, and that's great. But the environments don't need the exact same tools. pipenv seems to fix a problem I never encounter with pip/virtualenv during daily development work.

When I first got mac, I've spent the whole evening trying to install python3+pipenv and get it working properly. Ended up nuking system's python 2.7 and installing it through homebrew.

This was also frustrating me til recently. My imperfect solution is to use pyenv, which you can get through homebrew. Try it out.