So, it would seem that (barring human error) the primary philosophical difference between the packaging systems of OpenBSD and gNewSense is that gNewSense tries to prevent you from seeing any packages they consider non-Free, while OpenBSD directly provides only Free software (Packages) but gives the user a choice of installing any software (Ports).
The above description of gNewSense is inaccurate. gNewSense doesn't try to "prevent" you from seeing anything. How could stop you? What gNewSense does is avoid suggesting non-free programs you might use. The above description of OpenBSD is not false, but it is misleading. OpenBSD can't "give" (or not give) users the the choice of installing non-free software, any more than I could "give" you (or not give you) the choice of what to eat for dinner tomorrow. It's simply a fact that non-free software can be installed on any general-purpose system. The difference between gNewSense and OpenBSD which is the cause of my different judgment of them is that OpenBSD presents non-free software in the list of programs it can install for you (through the ports system), and gNewSense doesn't.