Things I'd like to automate:

• From tag to PyPi -- ideally, to test-pypi on every tagged commit (https://github.com/marketplace/actions/pypi-publish) -- and the actual release would be a special action I just click on. It's not that it takes a lot of time, but I'm always nervous I mess something up with the command line, forget to delete a file, git clean, etc. -- I very diligently work through the release-checklist to avoid that. Literally signing things off.
• Auto-formatting -- I tend to clean up the formatting of the lexers every time close to release, at least the worst offenders. I use autopep8 at the moment, would rather apply flake8 or black on the entire codebase.
• Auto-check that the new arguments like URL etc. are present on new lexers
• Auto-check .. versionadded:: is there -- costs me a lot of time to open up every Lexer close to release and make sure it's present and in the right format (i.e. 2.17.0 vs. 2.17)
• Actually get all checks working/passing (i.e. the additional checkers I wrote and possibly PyLint). check_whitespace_tokens and check_repeated_tokens need an expected-fail list so we can whitelist currently existing lexers until we fix those, but new lexers should always pass those tests.
• Verify all PR numbers closed/merged since last release are mentioned in the CHANGES file. I'm pretty good at assigning tasks to milestones now, but I still miss things in the CHANGES file, and it's super time consuming to open 100 tabs, go through each item one-by-item, check the PR number/issue number is present, etc. If there was a way to auto-generate the changelog that would be even better, but my experience is that those look pretty ugly and some manual checkup is fine.

I'll get to the release in a moment, thanks for the offer though!

Originally posted by @Anteru in #2576 (comment)