elitist punk answer follows:

um... you aren't going to be able to cover the entire problem domain effectively. (meaning, you aren't going to be able to cover each and every possible answer...) could I suggest you test for what is called boundry conditions instead? write a smart-ish system to analyze the datum, and figure out what the boundry conditions are (where if's flip, where buffers get overrun...) and test those, that would be the first step i would take in attempting to make a valid effort at software testing.

as a side note, i hope you understand how amazingly complex the field of software testing is, i had the amazing good fortune to study a bit under a man named roland untch, someone who taught me a great deal about software testing, just from the discussions that we had... his website storm might be of use to you, if you are interested in learing about this most amazing field... oh well :) that's that...