As far as I know (I could be wrong) you can only borrow points one year ahead, so to use points that he will be allocated on June 1, 2004, he can not "borrow" them until June 1, 2003. He may have already used or obligated all of the points from the allocation he will get on June 1, 2003.
If they were in "Holding Status" they wouldn't be available June 1 for a ressie in late Aug or early Sept - that is more than 60 days out.
Anyway, good luck on your ressie

As long as you're willing to compromise on the location, you'll probably be able to find a studio on property, and there is a good possibility you'll get lucky and get your first choice.
BTW, you know that all
DVC resorts, except OKW, have a "real" bed and a sofa sleeper in the studios? OKW has 2 "real" queen size beds - if it makes any difference. Of course, you can't beat BWV/BCV for convenience to EPCOT and Disney/MGM Studios