If we pretend for a moment that the OODA loop is different than the OODA process, and say that the OODA process is mostly structured as a series of time-steps, while the OODA loop is structured as a parallel circuit, with discrete paths running parallel with each other. Under this pretence, the advantage Venkatesh Rao is talking about is running on a different, but parallel, path than the example you talk about.
Although I believe that the math in Rao’s concept is flawed, the concept follows the strategic path.
The strategic path deals with structure, or form, that the loop will eventually take, and because Rao’s concept deals with structure (“executive decision” function) there is definitely an exponent. The exponent represents the structure of the loop and the exponent is the advantage of his concept.
The path of D&C does not have a exponent. Although D&C deals a lot with the culture of the loop which has an exponent, the model of the D&C path only says C=-D, so C+D=0.
In your example C+D did not equal zero, and that is the advantage of the incumbent.
In other words, if the incumbent force is in command of D&C, the advantage it has is the normal fact that the insurgency that is trying to control the D&C is never able to have complete command of the logic in the D&C, which leaves the OODA loop with a serial circuit.
This means the loop is left partially “open” in series.
I am not sure this is bad.
While it leaves open a path the “winner” doesn’t really want to leave open, the advantage represents growth (a well known growth) and, possibly, another way out, if your loop goes horribly wrong.
What’s Boyd say about that? If you are not will or unable to take the necessary steps to win, then you need to switch sides?
So while Rao’s strategy is trying to tear up structure, with the fight between who is in command on the straight-aways and who is in control at the corners, the incumbent advantage is leaving a door open, just in case Rao has his math wrong.