I need to think more about the rest of what you’ve said (and I don’t think it’s a short term problem), but I just wanted to point out that “managing keys” can be as simple as “create a secondary pass(word|phrase) and remember it/write it down/whatever”. It doesn’t need to be “secure this file and copy it around to all of your computers”. Likewise there’s no reason that “delegate authority to someone else” can’t be something like ``twine add-maintainer pip pfmoore``.