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> the benefits to users would be almost zero

Only if you just fix whatever breaks in the upgrade and never use the features in Python 3. The static typing benefits alone should either make your software more reliable (benefit to users) or speed up feature delivery (benefit to users).

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I’m on your side but what you refer to is not static typing and it’s not mandatory either.

You can get a lot of the benefits of static typing with mypy. I know it's not mandatory, my first sentence acknowledged that.

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