'Pretty' means, or meant,[of a quantity] 'great, considerable' . The OED says this is now rare except in 'pretty packet' and 'pretty penny'. This usage dates from the late C15.
My theory is the term may have come about because of the Illiteracy of the period Bit like what we did as kids Fred we'd swap things and try to get the Best not knowing what we gave away could have been rare then and priceless now We Did not read up on them until later in life (with education)
Returning to the Middle Ages Words and Numbers were meaningless to the common man, and a new coin was apparently a good thing to have Therefore a handful of shiny pretty pennies were a small fortune (Jackdaws and shiny trinkets also come to mind)
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