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Not having a story for interoperability between 3 and 2 was incredibly shortsighted. The migration path from Objective-C to Swift is an example of how to do this sort of transition right; Python got it wrong.

Widespread adoption of Python 3 would've happened years earlier if you could start a new project in Python 3 and not have to worry about libraries you want to use not supporting it yet.

The Swift 1->2->3 breakage has permanently poisoned the ever-important well of StackOverflow answers.

For some tasks, there are literally 5 mutually incompatible syntaxes to understand (Obj C, Swift 1234). Even though the UI can sometimes autoconvert for you, it doesn't help at at when you're looking at someone else's code.

Swift is a great example of what not to do.

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