The photo items are Marx but the subject is "real trains".
I grew up next to the busy main line of the New York Central near Rochester NY. I seem to recall that it was not unusual for some trains to have multiple cabooses. I don't remember any details of seasonal variations or if they occurred mainly in one direction.
Now I know in general terms that train crews, locomotives and cabooses might sometimes accumulate in one place and have to be deadheaded home. I would be interested to hear specific case histories of how and why this happens, especially on the old NYC.
There used to be car shops in East Rochester and perhaps some cabooses were deadheaded there for maintenance, but that's just a guess. Or maybe blocks of empty cars run in longer trains because tonnage is light. Does anyone have specific info on this subject?