Multiple caboose on a train - Model Railroader Magazine

DSO17:

     Some local freights ran with two cabooses. One on the hind end for the flagman and one right behind the engine for the conductor and/or the front brakeman. If there was a fireman on the job both the conductor and the front man could ride in the caboose, but if there wasn't a fireman one of them would have to be on the engine.

In the event a engine didn't have a fireman the head brakeman would ride the cab with the engineer.

Why?

Simple Union job classes..The conductor was not a member of the headend crew.The job of flagman was reclassified to rear brakeman with a job description clause to flag when necessary..This eliminated the job of flagman and shorten the crew to 5 men.

However,if a local was extra long a third brakeman was added to the crew to help the head brakeman do the switching.The conductor and rear brakeman would work the rear of the train.This in theory saved time.