Everyone who adopted python 2 on sizeable codebase is likely stuck there forever, with zero annotations and none of the new tools available, and they'll never be ported back.
But let's be fair, type related tooling in Python are not close to the ones you have in Java yet. It's just that eventually, everything comes around. Java got faster. C++ easier. Python ...toolier ? Etc.
Python broke all retro compatibility and put all existing sizeable software in a miserable deprecated state with the breaking of python 3.
I don't recall C++ getting easier. The few tools and IDE still fail at decent refactoring and code completion. The C++11 movement is adding few stuff more or less useful, piling on top of the vast amount of already existing complexity.