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The challenge is, at any point between 1516 and 1700, to split Naples off from the main Habsburg crown in Spain as a (quasi-)independent entity (similar to what a Habsburg Netherlands would've been). This would probably necessitate Karl V/Felipe II/Felipe IV to have more than two surviving sons (since I imagine that a second son would get Burgundy, while a third would get Naples).

My personal favourite would either be Karl V having three sons (D. Felipe II to inherit Spain; a second son to get Burgundy; and a third to get Naples) or Felipe IV (after Masaniello's Revolt) naming D. Juan José as king of Naples (Naples had been ruled by a bastard line before, so it's not unthinkable that Felipe might name JJ duke of Calabria - or somesuch).
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