Didn't read your first post today closely enough. Tried generating a .pdf file from the "Features" sample project. Same results:
Starting to build Printed Documentation...
Printed Documentation processor 8.0.1.204
Building C:\Program Files (x86)\Adobe\Adobe RoboHelp 8\RoboHELP\Samples\Features\HTMLHelp\!SSL!\Printed_Documentation\Printed_Documentation.doc ...
Preparing to create Printed Documentation...
Clearing output folder...
Preparing files for Print Document...
Copying files...
Updating files...
Finished preparing in 1 second.
Preparing environment...
Printed Document Generator Environment: Word 12.0.6545, OS 5.2.3790, RAM 3963 M Bytes
Building Printed Documentation 'Printed Documentation'...
Building Single Document 'Printed_Documentation.doc'...
Building 'Title Page'...
Building 'Table of Contents'...
Preparing to build chapters...
Building 'About this sample project'...
Building 'Topics'...
Processing 'About topics'...
Processing 'Overview topics'...
Processing 'Procedure topics'...
Processing 'Definition topics'...
Processing 'Reference topics'...
Processing 'Context-sensitive Help topics'...
Building 'Hotspot appearance'...
Processing 'Changing the appearance of hotspots'...
Processing 'Green hotspot without an underline'...
Processing 'Hotspot that doesn't appear "hot"'...
Processing 'Hotspot with different color'...
Building 'Images'...
Processing 'Using images'...
Processing '256-color graphics'...
Processing 'Default bitmaps'...
Processing 'Transparent bitmaps'...
Building 'Buttons'...
Processing 'About buttons'...
Processing 'Authorable button examples'...
Processing 'Mini button example'...
Processing 'Shortcut button example'...
Building 'HTML features'...
Processing 'About HTML features'...
Processing 'Standard commands using shortcuts'...
Processing 'Animated GIF Graphics'...
Processing 'GIF Graphics'...
Processing 'Time Java Applet'...
Processing 'Standard HTML'...
Processing 'ActiveX start'...
Processing 'HTML Table'...
Completed building chapters...
Building 'Glossary'...
Building 'Index'...
Updating list paragraphs...
Updating images...
Updating page numbers...
Updating page headers...
Updating Table of Contents...
Updating Index...
Saving 'Printed_Documentation.doc'...
Generating 'Printed_Documentation.pdf'...
Failed the generate PDF file 'C:\Program Files (x86)\Adobe\Adobe RoboHelp 8\RoboHELP\Samples\Features\HTMLHelp\!SSL!\Printed_Documentation\Printed_Documentation.pdf'...
Failed to save 'Printed_Documentation.doc'...
Cleaning up temporary files...
Internal error encountered, Failed to generate Printed Documentation.
Also, yes, I am using the html view to look for the "span:specialbold" tag. I was surprised to see the message in the output after I removed the only instance I could find from the seven topics, and--not seeing any other "specialbold" references--I searched each "span" tag. There are no "specialbold" span tags in any of the seven topics.
I just spotted Program Files (x86) in your last post. That implies you have a 64 bit machine. RoboHelp 8 wasn't supported on 64 bit machines. I believe it did work for a number of people but maybe this is one of the areas where it doesn't work.
Two options.
1] Uniinstall RoboHelp 8, check the PDF writer is removed as well and then reinstall. Maybe to find it has made no difference and maybe to find something more fundamental has gone wrong.
2] Live with the two step process. Generate to Word and then to PDF.
I would be sticking with 2.
See www.grainge.org for RoboHelp and Authoring tips
@petergrainge