Interestingly I was wondering if there were necessarily one "correct" answer to some of the words... some of them seemed to be more sentence descriptions and others the translation would depend on the point of view of the translator - e.g. terrorist, rebel or freedom-fighter... the versatility of the open answer was nice (a system similar to the name system in "Type Help" by William Rous might work?)
Either way, I have to admit that my suggestions are mostly for the benefit of others (if they want them) because I would probably turn them off... I really enjoyed it all as it was and was only disappointed by the shortness of the story! ;) - Also it might have been nice to add some parts of the tree that were essentially unrelated to the main line as it would have added a bit of difficulty or just a red herring for the main line game.
If you wanted to extend the story while still having the original in place or the expand the story sideways without making it too difficult to search up documents maybe it would be worth considering adding the ability to choose which generation's documents you are searching for (or some other count... I was intrigued by the season references but they didn't seem to add much information but if you could start the search from a particular date then it would give the player a reason to try and build their own timeline... it would also mean you could revert the document list ordering change ;)