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Is Python's tooling incredibly difficult, or am I just stupid?
(sh.itjust.works)
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You have been in lala land for too long. That list of things to do is insane. Venv is possibly one of the worst solutions around, but many Python devs are incapable of seeing how bad it is. Just for comparison, so you can understand, in Ruby literally everything you did is covered by one command
bundle
. On every system.