I think we tend to freak out over the calendar issue more than necessary. St Ambrose of Milan once said "When in Rome, do as the Romans do". I take that attitude when it comes to new parishes. I'm mostly New Calendar, but if the nearest, healthy, canonical parish is one that's on the Old, than so what? Sometimes in life we end up in places where we don't get the luxury of being picky about what parish we attend or what calendar they follow. Nowhere in the Gospel does it say or allude to our salvation being determined by what calendar we use. Christ said to love the Lord our God with all our heart, soul, strength, etc; and to love our neighbor as ourselves. He also said to forgive 77x7; which is an Aramaic term for "infinite". He did not say to follow this calendar or that calendar nor did He say to condemn those that don't follow your calendar.
Elder Cleopa says that if there is a judgment, it will only be for those who changed the calendar, not those who have been on it since.
Absolutely true. Elder Cleopa's monastery almost went Old Calendarist when he was a monk. Until the Theotokos herself appeared to the abbot reminding him of his obedience to the bishop and the need to remain united with his Local Church and not to cause schism.
Yes, I don't know why some want to give up traditions because "we are in America", "free world", etc. Muslims keep their small traditions regardless of the location.
The difference is that Islam is evil at its core. It is a cancer. It does not mean peace like they say. With how the word Islam works with Arabic grammar it is more like "peace via subjugation". Muslims have never truly abandoned the view that they are Muslim first, ethnicity second, locality third. They will always see themselves as being a completely separate entity separate from the rest of the world. That is a large part of why most of the Islamic World does not recognize the State of Israel: they still see that area as being "Muslim Land". Some even still see Spain as being "Muslim Land".
We Orthodox on the other hand, see ourselves as in the world, but not of the world. We are the hospital for the soul. We are here to heal and save souls. We are not here to conquer like Islam does.
I think the best thing all of us could do is acknowledge that the side we don’t agree with has a point, even if we think it the less important point.
As for me, I think those that favor maintaining the old calendar have good points. The points may be local - Greece and wrongful association of headscarves and the old calendar with the Ottoman Empire, but in those localities, they are serious concerns.
I bolded that part for emphasis because you said it better than I could.
There are practical matters to consider as well. For example at the Church of the Nativity in Bethlehem you have us, the Roman Catholics and the Armenian Orthodox all celebrating three different dates for Christmas. Roman Catholics on December 25, Eastern Orthodox Patriarchate of Jerusalem on January 7, and the Armenian Orthodox Patriarchate of Jerusalem on January 19 (other Armenians on January 6). I believe there is a similar setup for Pascha throughout the Holy Land. Either way, until the other Churches come back home to Orthodoxy, it isn't practical to have more than one of the Churches celebrate such major feasts on the same day in the same place; unless there is an agreement on how to do it; like when Orthodox Pascha and Western Easter fall on the same day.