Hi,
The main buzzword to think about in this situation is
maintainability. A help or training system created using an
industry standard tool provides a robust, maintainable system that
can be added to later.
The ability to single source multiple outputs from the same
master is a big plus and also you might want to think about the
capabilities of Technical Communication Suite.
Using standard tools makes it easier to find staff with
experience than using obscure tools. Word for example is simply not
up to the job.
In short proffesional documentation requires proffesional
tools and staff to produce and maintain it.
Just a few thoughts hope that helps