Agreed, the whole post treats Bob like he is some kind of asshole who needs to be destroyed for the betterment of mankind and advancement of the poster's power. How about buying Bob a beer and talking to him instead of running around behind his back and smearing him? If that doesn't work, ok, you can maneuver around him.
Odds are the whole problem is that he didn't have the time, resources and money to build what he wanted then other things came up. 10 to 1 says he never wanted to deal with a bunch of document files to begin with, that was someone else's preference and there was no web based WYSIWYG at the time that document person would have been comfortable with.