Completely with you, in complex projects the tooling can be improved and those tools attempt to do that. However going back to what the OP was suggesting about

Completely with you, in complex projects the tooling can be improved and those tools attempt to do that. However going back to what the OP was suggesting about how the situation puts them off using Python, I do think it's the messaging around this that's the problem. Python, the community, need to unify on a message around official tools. There will always be edge cases, but the noise generated by them can give the impression the ecosystem is broken when it really isn't.