Google can sorta already do #2 and what you are asking for is very hard in it's entirety. Wolfram Alpha is a great prototype but it also shows how hard it is to do in the general case. When Wolfram works it is amazing, but it often doesn't work. The problem is that there is too much ambiguity for the current state of the art of NLP and ML. However I do think it is possible to do what you are asking if you are able to constrain the context to one or a few major topics.
