mizzfit,
The VB comment still valid, uncertain as to relationship of to the following. I overlooked a clue here:

Producing an Optimized PostScript document...
I0012 : Error producing job of document "Statement.ptk": Out of memory while expanding memory stream
I0006 : PlanetPress Image output failed on host 127.0.0.1

http://help.objectiflune.com/en/knowledgebase/Default_CSH.html#/KB/ERR/PPI/ERRI0012.html

Remember, PlanetPress is a 32bit application and can only use about 3gb of RAM per process. Are the failing files very large?