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What if there was a clash between empires in the pre-modern era that caused the Aegean Islands to be the most fortified places in the world at the time? Is it possible?

What would be most interesting or plausible: a classical version as a stagnated Greco-Persian Wars, an early medieval version as an ongoing Arab-Byzantine Wars, or a Renaissance version with Venetians and Crusaders battling the Ottomans?
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