Milan is 9 hours ahead of Portland
Best overlap: 8:00 AM to 9:00 AM in Portland is 5:00 PM to 6:00 PM in Milan.
Target 8:00 AM to 9:00 AM in Portland, which lands at 5:00 PM to 6:00 PM for the Milan side. Milan is 9 hours ahead of Portland, so common hours are scarce (about 1 hour). Lock the slot, keep it short, and follow up in writing.