Where are the RMSs of the world?

Regarding the differential between FSF-free and OSI-approved, the examples I'm aware of involved licenses that were approved by the OSI but considered nonfree by the FSF. It is possible that those OSI-approved licenses, if reviewed by the OSI today, would not be judged consistent with the Open Source Definition. I believe history may explain this difference: at a certain moment in the past, the OSI seemed eager to approve certain licenses then being manufactured by the business world, while the FSF was eager to demonstrate its willingess to reject such licenses on articulated principle. I suppose that may be what you mean by 'institutional differences', but I would just emphasize the historical element. The two organizations were, to some degree, in competition with one another in that time period (I would not say they are today).

Disclaimer: FSF is a former client and I am currently an OSI board member, but I am just speaking for myself here.