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Welcome to our community, rschwarz100
I'm not sure I've ever seen RoboHelp automatically create a Table of Contents by pulling in a Word document. Maybe it's possible, but I've not seen it happen IRL.
Fortunately, creating a TOC is pretty straightforward using RoboHelp. You may launch a wizard to automagickally create one or you can hand craft one. Personally, I prefer to avoid the former and prefer the latter.
I am comparing the two myself right now, one of the things I like in RH for W is that Word has a grammar checker.
But there is one type of output that RH for W won't create and I think it is Macromedia's new style of web help...
I cannot add to Rick's statement, but I will address the claim that was made that RoboHelp for Word is simply RoboHelp X5. That's not entirely accurate.
RoboHelp X5 has RoboHelp HTML and RoboHelp for Word, just like version 7. I don't know how RoboHelp for Word upgrades, but I was able to open a RoboHelp HTML X5 project in RoboHelp HTML 7 with no problem (that is, after upgading to 7.02).
Not that this is likely to be important to you, but I thought I'd share.
Would that be the grammar checker that suggests changes that are nonsense?
RH for Word does create webhelp. I haven't a clue what you mean by "Macromedia's new style of webhelp" as Macromedia were taken over by Adobe a couple of years back. Could you perhaps mean Adobe's .AIR help? If so, the packager for that works on the webhelp output so in theory it should work on webhelp produced from RH for Word. Haven't tested that.
If you want webhelp, that is based on HTML better to create the help in an HTML editor such as RH HTML. Look at the posts in these forums where the problem has been caused by the HTML that Word creates.