But instead you use macOS?
You should give it a shot :)
1.) I absolutely agree on the Ubuntu front (though I don't believe for a second that things are better elsewhere. E.g.: Python on Windows is way worse in my experience). But I dislike Ubuntu (and Debian, for that matter) for many related experiences I had in the past.
2.) I'd say, though, that you're missing out on good containerization solutions if you're wrestling with Python installations on a server distribution.
3.) Most importantly: Where things like Docker or LXC don't apply (or don't apply as much; like development/desktop usage), the single best concept I've encountered so far would be the way NixOS and Guix handle installations. I sincerely hope that model will take off in the next couple of years. And I'm pretty sure that if it takes off, it will be on either Linux (most likely) or BSD.
Otherwise the fair comparison would be to a hackintosh, which would probably much more work.