If anyone’s interested, here’s an update, including a version with no tie pilot:
The ties come into formation by the end of the castle shot. The tie pilot stays in the middle of the forest fly-over shot because this is the drop zone. Before the shot, he has not scoped out the forest yet. After the shot, there is no implied space of time before the drop happens. To me, having him state that the drop zone is clear gives us a reason for the ties to be there in the first place, as well as connecting us to seeing the eventual troop drop.
Anyway, these are just my thoughts.
For now, this is my final sequence.
This is the same scene with no pilot.