strategy for booking two rooms at the same time

[Flossbolna]

If you get the reservation for less than 7 days on the 17th, then no one else (except those with 11 month HRs advantage) can book your room for any period of time until the booking period reopens on the 7 month availability open.
Example:
You are wanting two reservations for Oct 17th - Oct 21st.
On the 16th at 08:00 you book Oct 16 - Oct 22th.
On the 17th at 08:00 you book Oct 17th - Oct 20th, no one except those with 11 month advantage can book the 21st until 7 month booking window opens. Most 11 month booking people have already made their reservations, unless they are planning a last minute trip.
On the 17th at 09:00, you call MS, cancel the Oct 22nd, from the 16th reservation and use those point to add on Oct 21st to the reservation you booked earlier that day.

Yes, I think your logic makes a lot of sense - I am only confused as to why I would book to October 22? Shouldn't the first reservation be 16-21, then the second 17-20 at 8am and call at 9am to cancel 16 from first reservation and add on 21 to second reservation?

 

[supersnoop]

If you get the reservation for less than 7 days on the 17th, then no one else (except those with 11 month HRs advantage) can book your room for any period of time until the booking period reopens on the 7 month availability open.
Example:
You are wanting two reservations for Oct 17th - Oct 21st.
On the 16th at 08:00 you book Oct 16 - Oct 22th.
On the 17th at 08:00 you book Oct 17th - Oct 20th, no one except those with 11 month advantage can book the 21st until 7 month booking window opens. Most 11 month booking people have already made their reservations, unless they are planning a last minute trip.
On the 17th at 09:00, you call MS, cancel the Oct 22nd, from the 16th reservation and use those point to add on Oct 21st to the reservation you booked earlier that day.

That doesn't really hold true. You have no idea how many rooms are already booked in any given day. There could be two rooms on the 16, 17, and 18, but only one beyond that. Someone else could book at 7 months and take the last room in the +7 timeframe.

 

[Flossbolna]

That doesn't really hold true. You have no idea how many rooms are already booked in any given day. There could be two rooms on the 16, 17, and 18, but only one beyond that. Someone else could book at 7 months and take the last room in the +7 timeframe.

Yes, but I think the danger of that one room disappearing in the one hour between 8am and 9am for a later day is a chance that I am willing to risk. Of course, if it was already booked to start with, then no strategy in the world will help me. Also, as I said, I am more worried about the first nights of the reservation in my case, the last night should be a night that is less in demand (at least from my experience with reservation patterns in previous years).

I just wanted to thank everyone who has contributed to the discussion here! I love the DVC board as there are so many people who really understand all different aspects of DVC and are willing to share! This is definitely one of the most helpful boards here on the DIS and I learned so much on how to use my membership most efficiently!

 

[dcfromva]

If the other booking strategy doesn't work. I have had some success with booking the random days as they become available (assuming it is because of walking--there's a lot of movement just after the 11 month booking point). I WL other days. Then, I stitch together a reservation once I get consecutive days.

 

[Flossbolna]

I agree with this.
Book one room for up to seven days, on the 16th.
Book the other room for up to then number of days you want -1, on the 17th.
Then call MS at 9:00, to cancel off the 16th from the first reservation and use those points to add-on the last night of the 2nd reservation.
Once you have both reservations the way you want them, add in to both reservation a "Travel with" notation of the other reservation along with any special requests (IE: be near each other, be on opposite ends of the resort, etc).

I ended up using your strategy. And in the end it did not matter! I could have booked one after the other and I would have still gotten my reservation!

But thank you to all that provided advice!