The actual crossings are not really the issue--- its everything else. The language barrier / local procedures etc. If you have been there and done that before, you will be much safer.
That being said, it only takes a few times into any city, and you are then much safer going into that city.
Under "normal times" the requirement really does not matter, as whoever the new guy is would have a seasoned Captain to help. But with ANC being very junior, that seasoned guy is not a guarantee.
I do hate to see some overlooked because of the requirement though. I came from small airplanes myself, and did not really find it that hard to lean to fly overseas. However, I did benefit from some very seasoned Captains while gaining my experience.
Freig8t Dog.