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With Vista not supporting Winhelp is not true. WinHelp still operates on Vista. 16 bit WinHelp operates as it did before and 32 bit WinHelp requires a download, but still works.
However, moving to .CHM output is a step in the right direction.
Word was created to create paper documents. Later, it was used to edit Rich Text Format (RTF) files, that when properly marked up with the right code, created WinHelp files. Then along came the merry world of HTML and tossed a huge monkey wrench into the works.
If you use Word, it will create all sorts of unwanted "extras", that exist as a way to work around the limitations of the paper based world and create HTML pages. This results in all sorts of odd code and sometimes odd behavior that ends up affecting (sometimes severely) the way your HTML pages work and look. As you have seen, you usually end up with a mess of styles and formats.
If I were in your shoes (and once upon a time many years ago I was) I would move to RoboHelp HTML and drop Word like a hot potato. The WYSIWYG editor in RoboHelp HTML is very "Word Like", so you do have some level of comfort. To be very honest, about the only thing I truly missed after migrating the the world of HTML, was the Non-Scrolling regions. But now I don't even miss those.
Thanks for the feedback. I guess I'll have a nibble at the bullet sooner than later and see if it stops the problems we've been having. Seems a slightly retrograde step though, to lose the Word link. Oh well.