Classical art and discourse takes place in a network of symbols & ideas nearly completely lost to us. In art created less than 400 years ago, I'd say less than 5% of the content is accessible to your average university-educated person. Imagine in the case of archaic Greece.
Yes, if someone wanted a deep understanding, say, of the late 17th/early 18th century, they'd need to read a lot of memoirs and correspondence; and thence, tackle the literary works for a better understanding. Direct work with literary works produces A LOT of misreadings.
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This means there are serious shortcomings to just picking up Plato or Aquinas and having a go at it?
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Such material is simply not accessible for an author like Plato; you can read and study all that was written before him in philosophy in less than a year. I'm not too familiar with Aquinas' time, so I can't really say.
End of conversation
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