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Description
The idea: docs that take into account your setup and provide guidance accordingly. Can also provide advice on failures (of which vagrant up is prone)
Twine would be a good candidate for writing these sorts of docs given it's ability to mitigate complexity due to branching (usually for Interactive Fiction). It has some PL features that would help the cause of "damn good docs" as well.
Some example notes for quick start docs in this repo:
// choose your own adventure style.
// * choose 1. Quick, or 2. Deep
// * branch 1. Quick for prereqs needed or not... so on