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Any breaking release should only require a small amount of update work on the part of end users. Bundling too many breaking changes at once forces users to delay updating indefinitely. Make it as easy as possible for your user base to follow you, to evolve with you.https://twitter.com/GabriellaG439/status/1430201998045900801 …
The greatest asset of a language or framework is its ecosystem, and bundling breaking changes in a single release invalidates large swathes of your ecosystem. Always go with incremental change, so you bring the ecosystem with you. Evolution, not mass extinction.
Py2 -> 3 was incremental in the sense that most of the changes were mechanical, doable with 2to3 and only very few were significant changes, like str/unicode/bytes handling. And that change was long due IMO.
The people who build and maintain large production systems over long periods of time appreciate this stability and incremental change. Tough to build a palace on quicksand
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