just a generic comment if all the spots are not yet filled and it appears 5 applications, it could be safe to presume that each "leader/player" would or could be in charge of X # of the 300 which at the moment could be 60 each. looking at the map provided I can see spots where "scouting could render a way across, and other than by sea or around to the north the only other spot that I can see is a small pass way to the south.

@gm relatable question is do the 300 soldiers need to stay together or can the players split them up and go different directions ?