2, 3, and 4: we would be having our wedding in 2023 regardless, so those who could have made the Canada wedding would have the same amount of PTO to use if it were in Italy instead. Although they would still need to fly from UK to Italy, I believe they would save money overall given flights in Europe are much cheaper and they won’t have to make a separate trip to Canada at another time. The crossover is 30 guests from his family. There would be no hurt feelings if some members aren’t able to come given we are already legally married but still want to have all of our loved ones in one place to celebrate. My extended family isn’t close so I doubt they would travel to Italy for our wedding.