I'm not sure what benefit variety of background really brings to a squadron, where there isn't a lot of opportunity to exercise creativity. We're there, more or less, to operate a platform IAW a set of established procedures. It's not as though people are formulating policy or engaged in grand strategery. I think you may be overstating the value that NPS/Olmstead or even JPME would bring to an operational squadron. Personally (all else being equal), I would much rather have DHs who had maximized their time in the cockpit.
I think a fresh perspective from someone who has done something other than the very small standard set of tours, especially from someone who is apparently competent enough to get selected for a pretty competitive program, would definitely be of benefit to a squadron. Why do I think that? Personal experience from my first tour with EP-3's, where we had folks with a very wide variety of experiences in and out of the cockpit that helped us not only operationally but also with the professional development of the wardroom.