I have the impression that Wittgenstein's musings were of an informal, philosophical nature, and that they are difficult to translate to a practical real world

I have the impression that Wittgenstein's musings were of an informal, philosophical nature, and that they are difficult to translate to a practical real world application. That doesn't have to mean that he's necessarily wrong, just that for practical work such as in NLP you are forced to make some rather strong assumptions which are actually just wrong, but which allow us to approximate language to an extent where current technology can do something useful with it.