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Not just for beginners, the proposed syntax looks horrible in general. It's moreover already possible to put this into one line: libpaths = [] if libpaths is None else libpaths.split(":")
Yes, this PEP looks like it is trying to turn Python into Ruby where the ? suffix is common for a function that returns a bool. Also weird syntactic magic that you can't really figure out, you have to be told about. I wonder if the original author of the PEP is a "rubyist". Of course in Python [] is False and in Ruby it's true...
No, it's nothing like the Ruby convention. It's much more like th C# operators.