Here are a couple of workarounds for the crash in Windows.

The default stack reservation size is a field in the PE/COFF header, which you can edit using editbin.exe, e.g.:

    editbin /stack:[size_in_bytes] "path\to\python.exe"

The distributed python.exe has a 20000000 byte stack reservation. I changed it to 3 MiB and was able to run generated.py. You can also pre-compile it on a thread with a larger stack, e.g.:

    >>> import threading
    >>> from compileall import compile_file
    >>> threading.stack_size(2**20 * 3)
    0
    >>> t = threading.Thread(target=compile_file, args=('generated.py',))
    >>> t.start()
    >>> Compiling 'generated.py'...