There is a very wide middle ground between C++'s "Your horrific unsafe code from the 80s still compiles" and Python's "We changed the integer values common operations on strings return at runtime with absolutely no way to statically tell how to migrate the code".
In Dart, we moved to a sound static type system in 2.0, moved to non-nullable types in 2.13 (sound and defaulting to non-nullable!), and removed support for the pre-null safety type system in 3.0. We brought almost the entire ecosystem with us.
Granted, our userbase is much smaller than C++'s and the average age of a given Dart codebase is much younger.
But you can deprecate and remove old features without causing a decade of misery like Python did. You just need good language support for knowing which version of the language a given file is targeting, good static typing support, and good automated migration tooling. None of those is rocket science.