Google Maps and Waze are your friend, they should have reasonably up to date info. Keep your schedule flexible, as even a nominally open pass can still experience snowfall or dangerous rain and wind levels in May.
From Milan you always have the option of going across to Ancona and catching a ferry to anywhere from Split to as far south as Bar. I did that, coming back to Milan via Slovenia and the Stelvio Pass, which was open in June but had active skiing tracks at the top.
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