The riddle could have been asked at any time. I mean before the time of modern civilization and even most ancient ones.
Setting aside the anachronisms of ancient civilizations being able to comprehend a riddle in modern English, I suppose you mean that the answer is somehow contained within the riddle itself and does not relate to things in the modern world, as such.
1) Well, let's start with the obvious: THIS = THIS (thus THIS has to pay dearly). Some of those early riddles are that simple, but surely the answer has to be more clever than that?
2) Two failures might be two minus signs, and the meeting might be the vertical joint used in serif fonts that make the letter "I". The two they thought others would admire might be the two marks that make the letter "t", implying the possibility that someone, somewhere, for some reason might admire a cross. Thus we have the word "It", which starts the riddle: "
It starts with.... But ending wrong: when I see something wrong I *tsk*, which kind of sounds like "ch". So the wrong ending of "It" might be "ch", which gives you "Itch", in which case it is your skin that pays dearly with the rashes, and the abrasions, and the blood and the gore and the Moohaven-nyu-hay!
