I started to use python about 20 years ago, which was very pleasant (there was a nearly seamless transition from the old Numeric to Numpy at the time). I was using it less regularly for a number of years and came back to it to find what appears like an absolute mess.

Is there any good overview which packaging solution has which properties, and will work in specific situations?

and none of which work reliably

In fairness, many of these are open source and at least in the case of pip, for many years there was literally only two maintainers although now there a couple more. This is what I learned at one of the python conferences.

It’s odd how open source packages that big companies use can be reliant on so few people.

Edit: although checking the pip github, there more people committing so maybe I got something wrong, but there is far more activity starting around 2019.