One way to reduce the amount of reverse geocoding operations is to treat this problem as a search for the border. If you use a binary search algorithm, and reverse geocode each point, you find where the country changes from your current country to the adjacent country with a minimum number of reverse geocode operations.
In the binary search, your heading is constant, and you have a minimum range (5 miles) and a maximum range (12,000 miles), you are searching for the range at which the border lies. Then you reverse geocode a position just beyond the border to find out what country is there. One problem is that just beyond the border might be ocean.