I tried reading Beowulf in Old English, once, without ever taking a class in Old English manuscripts. Had to give up rather quickly. Maybe I am remembering wrong about the difficulty, or what I heard was from someone who had trouble with it, too.
It must be hard, the farther from the original, for translators to produce a work that is understandable to modern readers without losing things in translation, like they discovered with Shakespeare. I worry about Latin translations for the same reason. Some things don't translate directly, others are victims of word meaning changes (my favorite is egregious) or just plain obsolescence. Sometimes, translating passages or words is a matter of just getting the gist of it and saying it in your own words. I can see where translations can diverge some having to do that. And if you've read a particular translation, could that color the way you think about the passage or book when you try to translate it yourself? In Latin, translating a word can and does depend on the context of the rest of the sentence or passage. You really have to be on your toes. I never quite trust the accuracy of my translations, and on occasion, scratch my head at other translations.