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First of all, let's just assume that the Peninsula is united sometime before 1520 because Miguel or Afonso survive their untimely deaths, just to make this a bit easier.

The peninsula has always been full of land used for livestock farming, however that has the problem of eroding the little amount of arable soil there is and destroying vegetation, the latter of which only helps to accentuate certain regions lack of rainfall.
So, what sort of situation would be needed for a majority of those pastures to be replaced with land for farming?
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