We were able to get into the Boardwalk this year for the 2nd week in October, and we made our reservations in mid-June. We couldn't book earlier, as we just got our DVC points in June. We were looking for a Monday->Sunday, and initially were able to get everything except Thursday night at the Boardwalk. Apparently Sunday and Thursday nights are difficult due to the cruise bookings. The only facilities available on Thursday night were Saratoga Springs and OKW. So we got a reservation for Thursday night at Saratoga Springs and wait-listed at Boardwalk for the 1 night (and also wait-listed at BCV for the full 6-nights as another backup). About 3 weeks later, the wait-list cleared and we have all 6 nights at the Boardwalk now. We are in a 1-bedroom.
The only issue we've had is that the reservations are supposedly linked, but the dining reservations system only sees the first one.
You also need to monitor your wait-list status on the DVCMembers web site. You will eventually get notified that it has cleared, but will see as soon as it does on the web site.