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We tend to have a "Searching" topic in our Getting Started section of the help that handles the search syntax (e.g. use of boolean searches, etc.). Other than that, I'd have thought the install shield idea is a good one.
Before that, though, does anyone have any suggestions for working around the CHM search limitations?
If you can educate your users to add wildcards to their search terms, they can find all the words that you provided as examples in your message. For example, searching for auto* will find AutoComments, [Auto Release], [AutoCap], auto-run, and [Autocomment].
See this article for more information:
You talk as if the use of CHMs, WebHelp and .AIR are interchangeable.
CHMs are subject to security restrictions which mean that realistically you have to regard them as for installation on the local PC only. There are ways around but best avoided.
Similarly WebHelp is best when it is run from a server.
.AIR is currently for local installation.
So really your first decision is where you are going to install your application and the help.