In fact, even in real life, I suspect many one-boxers would two box in the end when they are standing there
My intuition says the opposite: I think many people who claimed they would two-box would one-box in the event. $1000 is so small compared to $1000000, after all; why take the chance that Omega will be wrong?
To wit: find that stone which I saw earlier and which I now recognise from the design that you showed me!
Ha, great theory. On the other hand, I find it hard to believe that the symbol was so obscure that even Voldemort never found it out. (Unless Rowling specifically mentioned it?)
What immediately occurred to me (similar to the infamous scene in The Princess Bride), is that if your opponent believes you will have a distraction and a real attack, simply lauch two real attacks, with the expectation that whichever one the opponent takes to be the distraction will succeed. Obviously this requires a greater sacrifice of materiel, but Quirrelmort doesn't exactly seem short in that department.
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I would say The Silmarillion is not very morally simplistic. Specifically I would call it Black and Gray morality [TVTropes], because I can't think of a single non-God major character who's totally good. (Maybe Luthien?)