Getting the same medal multiple times isn't sloppy. Getting them post-dated is, at least the way it's presented.
What you describe makes sense, but that's not immediately obvious to me as the user (one of many things in SH4 that aren't). It's mediocre interface design. Pretty common in games these days, unfortunately, but hardly a deal-breaker...after all, it's a sub sim, not a Navy Bureaucracy Sim.