You don't need to call day by day to get a reservation at SSR. I fyou are checking out on 10/28 (your last night is 10/27), just make one more call on November 28. If you are checking out on 10/27, then you can call on Monday, November 27 to book the whole stay.
Day by day calling is only necessary for certain times of the year or for certain room types at the smaller resorts. I can't imagine any room type or dates for SSR that would require day by day calling at the 11 month window.
IMHO, day by day at 11 months is a good idea for standard view or guaranteed Boardwalk view rooms at the BWV, Grand Villas/Beach Cottage at OKW, VB & BWV and
possibly the time between Thanksgiving and New Year's Day at VWL, and the Food & WIne Festival time for the EPCOT resorts. I'm not familar with HH, so it is possible that day by day is a good idea for the popular summertime reservations.
I would recommend day by day at 7 months if you want one of the smaller
DVC resorts - BCV, VWL or BWV.
Otherwise, you should be able to book your vacation with just one call.