After having a chat with the friendly engineer, I was told that the train wouldn't fit onto one track and he would need to break it down among a few tracks. He also told me that once this was done, he would not be proceeding down to Browns Yard, as I thought he would, but would be returning north to drill Bayway Yard before returning to Oak Island. Here, the train gets the signal to pull out past the signal before shoving back into the yard to split the train up.