[IanWhalen]

notmyname's mention of their process does reinforce one of the difficulties you'll have to address if you want to make a Bootstrap-like template - almost every company has a slightly different process.

OpenStack doesn't use GitHub for issues or pull requests, while MongoDB doesn't use their issues but does use pull requests. Some projects require you to sign a contributor agreement, some don't. Different languages (coding standards), different platforms (testing), etc. So you'll probably want to bake the customization aspect (a la http://twitter.github.com/bootstrap/customize.html) into the very core of your idea.

As for examples: - the guidelines for the MongoDB project (not bad, I think) are here: https://github.com/mongodb/mongo/blob/master/CONTRIBUTING.rs... - and the Contributor Guidelines for Chef are quite good too: http://wiki.opscode.com/display/chef/How+to+Contribute

[pessimism]

I was thinking about something dynamic and interactive with dialogues like “Does this apply to you?”, where people can click Yes or No.

Because you are entirely right, and there will never be a one-size-fits-all file. That’s why I am thinking about a solution that instead uses one-size-fits-all questions that people have to ask themselves, and these could dynamically either create the guidelines outright or prompt the authors to think about the question for themselves.

As my own guidelines highlight, you inevitably veer into subjective style guidelines, and we all know how long people can go on endlessly about JavaScript style guidelines.