Suppose Charles V decides rather than recognising John in his will as he did OTL, he legitimises him before his death and have him rule Milan instead of Philip II. How does this affect Italy, the empire, and whom do we propose Juan weds? Would it be someone from France (double wedding maybe Claude of France or is that too much for an out of wedlock prince as part of the peace of cateau-cambresis) or someone from Italy (Guila de medici, also out of wedlock but related to the Medici's who would regain the papacy later in 1559 https://en.wikipedia.org/wiki/Giulia_de'_Medici)