I understand that this "positive will of organizing" is related to legibility in the sense of James C. Scott (see e.g http://www.ribbonfarm.com/2010/07/26/a-big

I understand that this "positive will of organizing" is related to legibility in the sense of James C. Scott (see e.g http://www.ribbonfarm.com/2010/07/26/a-big-little-idea-called-legibility/ http://www.ribbonfarm.com/2010/07/26/a-big-little-idea-calle...). But this failure mode is so common, that one would think that it would be in mergers and acquisitions textbooks already! As you say incentives may play a role as well, but I think it is very common that large organisations never actually consider the option of not organizing something, in this case, letting Nullsoft do their billing whatever way they wanted at first, and integrating it later once it is stable enough to allow a complex development project. To lead an organisation, one has to know what is happening in it - This has a complexity cost, which should be explicitly managed. New acquisitions would need to be treated differently, and full assimilations into the acquirer may not be a good result at all.