Wow, that's a tough one. Some how you need to translate imprecise language into precise computer logic. If I remember my AI courses correctly(seriously, that's a stretch), you'll be going down the road of AI and machine learning. Unless you build thing really amazing, I think the best you can hope is a "guide", rather than something terribly useful.
Like Choad eluded to, maybe a simply statistical based system is a good start. I just can't see anything simply being worth anything.
Sorry, I wish could help more.