I think the writers they had around in the first season of TNG just really sucked.
In fact, pretty much every first season episode I actually liked has the Maurice Hurley writing credit.
I could write an NLP program that can use contractions. Heck, I could practically do it in one line of code. str.replace(/can not/g, 'can\'t).replace(/will not/g, 'won\'t').etc. Data can interpret the exact meaning of complex grammar. I think Soong could manage that one line of code.