We would be remiss not to call attention to the original HTML Help transform that has been bundled with the DITA Open Toolkit for several years.
Output from the DITA Open Toolkit HTML Help plug-in serves as input to the Microsoft HTML Help Compiler. If you choose to build your DITA sources on the same Windows system on which you have installed a copy of the Microsoft HTML Help Software Development Kit, you will be able to generate a ready-to-deploy MS HTML Help .chm library from your DITA-OT ant script. Otherwise, you an copy output from the DITA Open Toolkit HTML Help transform on your DITA-OT build system to some other Windows system on which the HTML Help SDK has been installed.
Once you have installed and configured the DITA Open Toolkit, you have the HTML Help transform installed by default and ready to use. See the DITA Open Toolkit User's Guide for detailed information about working with transforms and about specifying the HTML Help transform specifically as a processing target (dita2htmlhelp).
To download the latest Microsoft HTML Help 1.4 SDK, go to the following MSDN web site. It is a free download.
http://msdn.microsoft.com/en-us/library/ms669985.aspx
To generate ready-to-deploy .chm libraries from most any DITA source collection, you do not really have to customize or rework your DITA source files.
Truth be known, there are also limitations to both this DITA-OT transform and to the MS HTML Help run-time environment. Factor these into your planning.
The .chm library produced by the combination of the DITA-OT HTML Help transform and the MS HTML Help compiler is very functional.
Here's what output from the DITA-OT test collection looks like.
If you have requirements to deploy a general-purpose Help collection to Windows customers without context-sensitive integration, consider using the DITA-OT HTML Help transform. It is functional, reliable and fast. Once all your content in is .chm format, you can convert it to other distribution formats with second-tier conversion tools such as chm2web. If you have requirements to integrate .chm output with Windows applications as Context-sensitive Help, you'll need to invest some time managing maps and alias files outside the DITA environment and then integrating them with .chm output using WinAnt or other custom processing environments.
Stan Doherty
Individual
OASIS DITA Technical Committee
OASIS DITA Help Subcommittee