I come here as a former military officer who served during the Reagan administration not to praise him, but to bury him.
In some ways, Reagan was good for the military. He certainly ensured that more money was pumped into it; the direction was often useless, but that's inevitable. More importantly, he presided over the thankfully quick tenure of Korean War lieutenants as four-star flag officers—and did a reasonably good job keeping them in check.
However, that's about it for the good points. I do not believe that Reagan's approach—or, more properly, the approach of the people he trusted to run the military—was good for the officer corps. I watched younger officers come in as if they had all passed a litmus test, particularly by the late 1980s. I watched total disdain for officers whose missions were not anti-Soviet wreak havoc on promotions and morale. In the Air Force, I watched the return of the arrogant, narrow-minded, leather-jacketed fighter pilot as the role model for officer training. From the outside, I watched the Navy, the Marines, and to a slightly lesser extent the Army rush down similar paths to tunnel vision (the Army didn't really gather momentum until George II).
Most particularly, Reagan and his advisors had a tendency to put people into jobs for which they were not qualified and then express surprise at their failures. Perhaps the most obvious example is VAdm Poindexter and Lt Col North—neither of whom had the tiniest bit of experience dealing with either Southwest Asia or Central America. This is not to say that experience is all; or even that experience is the most important factor. However, when everyone with experience is repeatedly passed over for promotion and for jobs for which they are the most qualified, they tend to get fed up and leave. That is precisely what happened. This results in an "experience vacuum" among the decisionmakers. Of course, there's a long tradition of this; the Carter folks, on balance, weren't a whole lot better, and George II's cronies were actually worse.
The President can't do everything himself. For that reason, I think commentators who look only to the top of the heap to measure "greatness" (or, for that matter, "mediocrity") do themselves a disservice. Looking at the people around President Reagan in retrospect does not inspire confidence in his ability to pick the right people for the right jobs. Poindexter/North is not a fair direct charge, because Reagan didn't appoint them. He did, however, appoint such luminaries as Edwin Meese. The personality flaw shared by so many of these people is one that simply cannot be tolerated at high levels in government, or in the military: refusal/inability to recognize or accept responsibility for errors. That's where we got "plausible deniability." In turn, that wormed its way (quickly) into the officer corps.
And so, we're back where we started. My commissioning group now includes a mix of lieutenant colonels and colonels, along with a couple of flag officers. In the next couple of years, some of them will achieve flag rank. We were lieutenants and captains during the Reagan administration. I'm not all that thrilled by that prospect. Along with everything else—his role in cooling and ending the Cold War, the generally bright judges he appointed, and a few other positive aspects—this is part of his legacy. We'll learn exactly what that is during the next decade or so.