He has 2 safety schools. He put one of them as his #2 school on the list. The other one is #6. I fully expect that even if he is awarded a scholarship after the upcoming board, the # 6 school will pass on him. Who knows even the #2 school may pass on him, seeing that #1 school is a reasonable option, as in, if my son gets the scholarship, he is likely to get in, and as such, the PMS of that school will pick him.
I think you have a very good strategy here with the safety at #2.
If #2 school is a place that doesn't get a whole lot of interest from candidates selected at the early board and mostly fill their scholarship quota from later board candidates, they have little to risk in giving your son the
and offering him a scholarship. If he declines, the scholarship will be recycled through the next board, so they won't lose the scholarship. If he says yes to the safety school (perhaps #1 had too many great candidates and didn't give your son an offer), they've got themselves a superior scholar (at least on paper - the real test comes on campus) that they wouldn't ordinarily get.
Don't underestimate these PMS'. There is a high-stakes game being played here trying to get the best candidates they can, risking the candidate who turns in his/her scholarship at the end for a WP appointment (at least in the case of the OP). They want to say yes to the list of candidates who are most likely to say yes in any board (I believe they can change their yes/no decision between boards).
I can tell you that with goaliegirl's situation last year, we had to coordinate ROTC priorities with hockey recruiting priorities, so explaining that the list originally submitted in September were based upon the potential playing opportunities along with the desirability of the school. When school #1 went dark on the communications from coaches (and the unit for that matter) along the way, that was clearly communicated down the list. I believe that had a lot to do with the scholarship offer she received and accepted.
In the end, everything has worked out very well. Goaliegirl has made the hockey team (tryouts last weekend) and has excellent prospects for playing time as a freshman (unusual for frosh goalies). She is in a ROTC unit that has been very supportive of her athletic endeavor and is having a great all around experience at the school so far. My wife and MIL just returned from parent weekend (neither had been to the school before whereas goaliegirl and I had been there 3 times before enrollment) and can confirm that she made an excellent choice.
Message to OP - You can balance potentially conflicting goals if you have a clearly thought out plan and communicate it honestly and effectively to the units. If OP's son has applied to WP and isn't entirely 100% committed to the academy experience, he needs to define the decision process (what steps and when?) and communicate that to the units on his list. The candor will earn you some points even with the most competitive of PMS'. They would rather deal with a certainty than a game of chance. Definitive dates and priorities help reduce the uncertainty in their minds.
I think the PMS' message was a check to see if your son has a clear decision tree. He is working under the assumption that WP is a strong #1 in your son's mind. That is probably the case for most WP applicants, but not all. Whichever way he leans, it should be made entirely clear to the #1 school PMS. Even if WP is #1, it should be made clear. You will get the PMS's respect. And if WP doesn't come through (these guys aren't perfect at predicting success) and you want to transfer a scholarship from another school that gave you a chance, you might be at the top of the transfer list in April.
Make his intentions clear, but if they are not clear, at least make his decision process clear. It will serve him well now and throughout his career.
Best of luck.