The following are my suggestions regarding what else to consider for each of Daryl White’s excellent questions about choosing a toolset for documenting a software product or project.
I have appended a brief guide to the main/broad categories of documentation toolsets and some of the platforms/components that are popular in each.
Finally, this resource ends with a table of possible solutions for various scenarios you might find yourself in.
Before we start with the existing list of questions, I want to highlight one that I think is most important of all, but which is often assumed by people who create these kinds of guides, as they tend to come from one or another world already.