Say I have a software project for which the technical documentation should includeA license documentA list of used terminologyAn introduction about what the software doesA short quick-start guideComplete documentation of tools covered by the projectDocumentation of file formats and protocolsAn API ReferenceA list of known bugsA todo listA set of examplesWhat is a good order of these points?How can these points be organized into chapters, sections, subsections, and subsubsections? One of the tools has an hierarchical configuration structure. Should this structure be represented in the documentation outline (this will result in a really deep outline) or should it be flatted in some way?
Outline for technical software documentation
documentation
For this kind of projects, where software products requires large documentation, you should better not include all the information in one single document. A good approach to this to have a Workbook for developers which is a set of different documents directly related to the software product. You may structure your workbook so that it includesA licence documentAn introduction about what the software does,a short quick-start guide,complete documentation of tools covered by the project,documentation of file formats and protocols,an API Reference, in one separate documentThe lists of known bugs and todo list in another documentA set of exampleThus you will have 4 different documents in your workbook. You will have to name them so that developers could easily  understand the content of the document.Hope this helps