You can use type hints with Python 2 in the form of special comments (http://mypy.readthedocs.io/en/latest/python2.html#type-check...). Guido has been working on the type hint project for dropbox specifically to help them to migrate 2.7 code to 3.

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.

Java got faster and got some functional features.

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.

C++11 makes a LOT of things much, much easier. Yes, it does pile on top of existing complexity because they're loathe to eliminate any backwards compatibility, but the nice thing is that you don't have to use older features or methods of doing things. In fact, if you look multiple serious C++ codebases, it'll almost look like they're different languages, as every project basically chooses a subset of C++ they accept. Realtime embedded code doesn't look anything like desktop application code, for instance, but they're both technically C++.

And as far as I remember even google is only supporting python 2. Their python-go transpiler doesn't support python 3 for example (unless something changed in the last months and I missed it)

Most of the C++ annoyances have already been fixed by Dlang, which interfaces very nicely with C/C++ libraries and code.