Hi Orin,
I have tested this in several versions of Thunderbird: 
52.9.1 (64-bit) 
57.0b2 (64-bit) 
60.0 (64-bit) 
I get the same result as you do.
I will report to Mozilla on this.
Thanks for detailing the steps.
:)
G

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https://bugs.launchpad.net/bugs/509665

Title:
  Printing multiple messages to file, gets overwritten

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