1. Have you ever tried personal initiative but you were shot down by "higher ups" because the FAR did not authorize something? No, not that I can remember - my contracting world is not that complicated that it falls outside the regulations/policies/EO... found elsewhere.
2. Have you ever used personal initiative and your idea was supported by "higher-ups?" See above
3. In federal contracting, is it easier to be human or to be an automaton? Have to agree with what's been said above (with the exception of CDS who apparently has found a utopian contracting office for which I am jealous). In my experience, I see a huge push to homogenize the federal acquisition field - make all documents and contracts look alike. That's best accomplished by automation. Human thought wreaks havoc on automation.
4. If you answer automaton to #3, is it because of GAO protests, supervisors, etc? To a degree, yes. But it involves much more than that.
I have actually seen this FAR principle abused rather than properly used because the individual ignores the principle in its entirety and thinks that if the FAR doesn't prohibit it, it can be done, but fails to take the additional step of researching whether the action violates other regulations, laws or policies.