I think it is somewhat hindsight bias to think Alexander would even care about Italy. Alexander was concerned about conquering the Persian Empire which was vast

I think it is somewhat hindsight bias to think Alexander would even care about Italy. Alexander was concerned about conquering the Persian Empire which was vastly larger and more wealthy than Italy. At the hight of the Roman Empire, the richest areas were always the former Persian areas - Egypt, Syria, Anatolia. This was also the reason the Roman empire ended up moving the capital to Constantinople.