As to the half marathon date mentioned above, the addition of the extra week in Nov for Food & Wine was announced very recently; the half marathon cannot change to the later weekend, at least for this year, because it was set some time ago to allow runners to register.
As to the 7 night rule, you can book only 7 nights if you are booking exactly 11 months (home resort) or 7 months (other resort) from date of arrival. If you waited some days past the exact 11/7 date to make the reservation you could book the entire stay at once for that Oct and Nov time, but waiting to reserve could easily mean the difference between getting the reservation and not getting it.
As to booking home resort, it would be a good idea to do that for the entire stay, not just the last two nights, to assure you will have a place to stay. You might set it up as two reservations, one for the first seven nights and one for the last two so that if you find OKW open at 7 months out, you can cancel the first 7 nights at your home resort and reserve OKW and then wait two days and call to add two nights while cancelling the second reservation, or even make three reservations, one for the first seven nights, one for the eighth and one for the ninth night, which would allow you to call daily after getting the first 7 nights at OKW and make a change. If you go with the multiple reservations, it is important not to have them linked before you try to make the change at 7 months out because linked reservations cannot be cancelled online until they are unlinked, for which you would have to call MS to do, and thus lose the one hour online reservation advantage.
