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<p>Nah you just need the one caboose. I'm pretty sure they would cut the caboose off on the mainline and have a flagman to protect it. After dropping off the car to be spotted, they'd pick up the caboose and continue on their trip.</p> <p>If a train had more than one caboose it was usually because one was a Drover's caboose on a livestock train hauling a crew of cowhands to help with loading and unloading livestock. Another case for multiple cabooses on a train would be a particular yard accumulated too many cabooses from elsewhere and was sending them back to where they're needed. Only the last caboose would contain a working crew. The others would be empty and those crews would have rode back to their home terminal on a passenger train.</p>
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