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Is Python's tooling incredibly difficult, or am I just stupid?
(sh.itjust.works)
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Are you sure? I'm not very active in that ecosystem, but if that was prevalent in the past, surely there's still tutorials and stuff out there that people would follow and create such projects even today?
More than that, it seems to me that the official python docs for packaging [still] talks about setup.py. Why would people not use that?
Sure, there was some hyperbole. Some people need some specific setuptools plugin or something. Almost nobody.