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I think cherrytree might be what you are looking for. http://www.giuspen.com/cherrytree/ You can insert check-boxes (Edit->Insert special character) and tick them or untick them with a click. http://www.giuspen.com/topic/cherrytree-on-mac-osx/ The image is from Linux, but it's also available for Windows. I don't see it for OSX, but somebody got it ...
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