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I get this question from time to time. Here's my most recent response, dusted off and updated:
A few of us in my organization have been using Flare for awhile now. We're quite happy with it. We began using version 1.1 in May 2006 and have used it for three good-sized software projects, one of which has shipped to external customers and one of which is about to ship (both of these used compiled HTML help). The third project is internal-only; you can see our Flare-generated web help for that product at [deleted cause it's internal]. (We also generate .chm files that get installed with the software, but the web help is nice for an internal product; we can update it more often that way.)
We recorded some observations for another team that has since adopted Flare:
* Some annoying defects in RoboHelp were fixed in Flare; the ones that come to mind (this is based on my experience with RoboHelp X5) are poor PDF output, some bugs with merging multiple help projects, and lack of command-line build capability (so it's hard to integrate your help into an automated build process). Flare provides a nicer authoring environment and more consistent results (once you're used to it) because of its use of structured editing and emphasis on stylesheets; the XHTML source it produces is less noisy (hence more portable) than RoboHelp's HTML. More importantly, RoboHelp is an aged product with a very large code base and an R&D team that have no history with the product; Adobe's commitment to the product is real, but seems weak. Flare is more robust because of its managed-code code base and is staffed with experienced (and enthusiastic!) developers; Madcap was founded for the purpose of creating help-authoring tools and Flare is its flagship product. Flare is at 3.0 now and is very stable. It does a very good job of importing RoboHelp projects and templates.
* Excellent Support. Both through the help community and when I've escalated issues with a support ticket; I've always received reasonably timely assistance.
* Regular new versions with innovative features. This includes, for example, the Feedback Service, Topic Tracking, import/export to FrameMaker, etc. Even though I haven't used these features (yet), I am impressed that Madcap has developed them.
* For intents and purposes, I was a first time user with no (within the last 10 years) Robohelp experience. I found it very easy to learn and use Flare.
* Some things were not as I expected, such as importing XML code samples into a topic, and some things are a little quirky, such as the red/yellow control boxes and cursor size significance, but again, overall I found it very easy to learn and use.
* It is stable (no crashes), importing existing RoboHelp files was very easy, search capabilities are great, it has a rich feature set, etc.
* Command line build is very easy (though it doesn't report all errors).
If you're buying, it's worth paying for bronze-level support: you get free upgrades that way, and they're upgrading rapidly (went from version 1.0 to 3.0 in 15 months).
We didn't really take a quantifiable schedule hit learning Flare. You feel sort of dyslexic using the structured editor at first; you don't always know what you're looking at, and basic things like text selection don't do quite what you expect. We stopped complaining after a week or two of steady use. Everything else is quite natural, and if you can't find a feature, you can search their help using the RoboHelp terminology and easily find the Flare equivalent. We've brought in contractors who had experience with other HATs but not with Flare; they've had no trouble picking up Flare quickly.
If you haven't browsed the user forums at www.madcapsoftware.com, take a look: there are lots of real people using Flare and talking about it. The Madcap folks I've contacted via support, the forums, and at WritersUA in 2007 really seem to speak our language and understand our needs.
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