I ran into a 36 inch section of 027 track years ago that would only short out if it was deflected slightly. So the weight of the engine would make it short out. I had never seen that either before or since. Also, you mentioned a lighted caboose, I have seen those short out intermittently sometimes. My suggestion would be to just take the caboose off and set it aside and run the train for a while without it and see what happens.
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