Pennak; I understand your desire to be ahead of the power curve; hence the analogy of being 10 moves ahead. But that is not going to be possible in this scenario. The best advice anyone can take, is to have alternate plans. The same advice we give our applicants when they are initially applying for the academies or ROTC. Have backup schools. Assume that you WON'T get an appointment or an ROTC scholarship. Plan everything around that assumption. Plan for the worst and pray for the best.
Scholarships are no different than any other contract. Granted, they are year to year, but I doubt that any budget cuts are going to affect current scholarships. Personally, I believe that the education being obtained is the most important thing. These young people were going to go to college anyway. Chances are, it's not like "If you don't get an ROTC scholarship or an appointment, then you have to work in the coal mines". Matter of fact, the majority of ROTC students at our state university, are in ROTC WITHOUT a scholarship. They have other scholarships, loans, grants, etc... but not ROTC scholarships.
That's the only plan you can make. Plan that there are no scholarships. That's what we did. We assumed that my son wouldn't receive an appointment or scholarships. Now that he HAS, and is getting ready to graduate in May and get commissioned, we have a lot more disposable income to do as we please. Now, if an individual's college is based entirely on an existing scholarship, I don't know what to say. Even my daughter, who isn't military at all; "Meaning she went to traditional college/university"; she had scholarships, but we assumed that they would NOT be renewed at the end of each year. We planned for that. Those were the 10 moves ahead that we made. Each year, she had some scholarships renewed and then loved the dorms and became a resident adviser; which provided her with free room and board. More gravy for us. When she graduated in 2009, we had even more disposable income. But we were prepared to pay for her entire education if necessary. That's what our plan was. This may not help you directly, but hopefully anyone else in the planning stages of their child's education, will Plan for the Worst, and Pray for the best.