Webhelp Pro output is ONLY required if you have RoboEngine
(now called RoboHelp Server) installed. The output type allows you
to publish to a server and generate reports on the help's usage.
From what you say, webhelp is the way to go so you can leave RH
Server out of the equation.
As far as the settings are concerned, try the "local pc or
intranet" option as this is specifically designed for intranets.
BTW phrases like "the company's cranky infrastructure"
doesn't instill confidence that anything you try will work