From my perspective Devon has three options I’ve added to his indoor plan below. No I’m not suggesting he turn him into a buoy with two of those locations.
From what I know of Bob he also enjoys ships and watercraft, so why not position him where those things meet on Devon’s pike.
A. He could be standing on the land/dock and watching/guiding a barge/car ferry into the track connection.
B. He could be on the barge/ Car ferry.
C He could be on any other type of vessel that is docked up along side the dock spur. You know that tall ships could have a crane rigged in so that they could actually off or on load items from a dock, or in this case a flat car.