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I'll be happy to answer as best I can and hopefully others will chime in to fill in what I'm unable/unqualified to answer. You didn't say which RoboFlavor you are planning on using (RoboHelp for Word or RoboHelp HTML) so please know that my answers are related specifically to RoboHelp HTML.
1) The ability to create text on top of a graphic?
This is possible, but may not work as you would think. When I think of placing text on a graphic, I think of opening the graphic image in an image editing application such as Microsoft Paint or Adobe Photoshop or Fireworks. Then placing the text where I want it and saving the modified image where the text is actually part of the image. But you actually *CAN* accomplish this by using Positioned Text Boxes in RoboHelp HTML.
2) The ability to add comments to the output file?
Using a workaround and some "outside the box" thinking, sure! But there is nothing in the RoboHelp application that would directly facilitate this.
3) The ability to merge changes from different users to the same output file?
Hmmm, this won't be possible if you are talking about the RoboHelp output file(s). But if you are talking about the source files used to create the output, you could accomplish it by either using manual source control or a source control application. RoboSource Control ships with RoboHelp and you could also acquire Microsoft Visual Source Safe (VSS) separately.
4) The ability to go from one page displaying in Protrait, the next in Landscape, and then back again to Portrait, all within the same document?
I'll have to defer that one. It sounds like you are referring to creating printed output. I tend to avoid creating printed output if I can. I take the stance that it's called "On-Line Help" for a reason. And, there's that silly notion about actually liking trees.
5) Templates or Style Sheets to work from?
RoboHelp HTML supplies a few pre-defined style sheets you may use. You are also free to import or create your own! As for templates, these are easy to create using RoboHelp. However, there aren't any pre-defined templates I'm aware of.
6) The ability to do conditional text, or tagging, for specific versions?
Ab-so-freakin-lute-ly! In the most recent version, conditions may be applied to entire topics, text, images and objects inside topics, TOC nodes or Index terms. And to go even further, version 6 also offers variables, which can reduce (and in some cases eliiminate entirely) any need for conditions.
What is the learning curve for the software?
Personally, I think the learning curve is pretty easy. RoboHelp handles all the heavy lifting for you and shields you from having to know any coding that is needed behind the scenes.
If you are interested in training, I'm also an Adobe Certified RoboHelp and Captivate instructor. I'd be happy to try and hook you up with some formal training.
Hopefully this was helpful... Rick