Below, is my reasoning for the placement of the tie pilot shot. I tried things in different orders but it kept coming back to this (which, personally, I really like). Still, I don’t presume to think that there is any single correct sequence. If others end up using any of this, it will be cool to see all the different versions they come up with.
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.
I might give the other shot you mentioned with the ties coming at the camera a try at some point.
Thank you again for the great tip on optical flow!