The downside to pipenv is that there aren't any good docker images to work with it. I've tried a few times, but I've never given enough time to learning the guts of Docker to make anything stable enough to run with it.
That shouldn't be too much of a problem. I'll have to port an image over later to use pipenv, so I'll share a gist to a minimal Dockerfile.
I did, but something about Alpine rubs me the wrong way. I know it's probably irrational, but my gut always goes to Debian. I really can't justify it. Maybe I should give it a better chance.