I suspect it's an issue with the operating system (as you cannot replicate on a different server).
What does the script where it fails do? Is there really a huge memory allocation by the Workflow services at that moment?
It sounds to be an issue with running too much scripts at the same time.
Does it happen even with a small single data file?
I don't think it's an issue with PlanetPress itself, but you may try to repair PlanetPress just to be sure.