I find that the mobile app fares better. On the iOS version, it was able to get various visual novel characters first shot, but the web version failed (at this point in time). I am curious why they are not using the same database. The iOS version also appears to ask less questions and get it right. Another thing I noticed is that it appears to follow trends. I mean, asking if the character is handicapped directly after I confirmed it was a high-schooler...
Update #1: It asked if my character had yellow skin... no, you racists.
Update #2: It asked three times if it came from a korean manhwa... I already said "yes" damn it!
Update #3: It is fairly easy to win (in my perspective). Just choose something very obscure, then choose a minor character. Because trust me, you are never the "only one" who knows about a certain series (for the most part).
Update #4: It appears not to care about the relevance of its questions. After I confirmed it was from Touhou, it proceeded to ask completely unrelated questions.