Booking six months in advance, the odds of a desired room being grabbed during the time it takes to go from one completed reservation to the next is pretty much like the odds of being struck by lightning. Yes, it could happen, just like someone could by a MegaMillions ticket and be the big winner. There is a greater chance your #1 choices could be taken during the time it takes to get answers here.
Just pick up the phone, call the AGR customer service number (1-800-307-5000), and book both the paid and award reservations. There will not be an issue.