How can I troubleshoot
"The Printed Documentation Wizard encountered an unexpected error when attempting to generate Printed Documentation"
using Robohelp HTML 10.0.0.287
It did create an output file, but I don't know if it's complete.
It created a log file in output directory that only contains:
That suggests a problem with one or more topics. I'm puzzled by your comment that you don't know if the document generated is complete. It is unlikely a document was produced but if it was, then looking at it would tell you if all the content is complete.
See www.grainge.org for RoboHelp and Authoring tips