wi: Isabella of Aragon, daughter of Isabella the Catholic born male

If Isabella of Aragon is born male, in this time he is called as Juan, he can marry Juana La Beltraneja instead of Alfonso V of Portugal, solving the Castilian succession issue.
 
This could stave off succession troubles for the time being, but there's still the possibility of a war between both Iberian kingdoms over the West African islands and trade outposts, unless a personal union is conceived.
 
So Isabella & Ferdinan either:
a) marry their oldest son and heir to bastard.
or
b) acknowledge la Beltraneja as rightful heir of Castilian throne
 
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