elfbo said:
1. Do I have a chance of getting a standard view room in october?
There's always a chance. Depends on how many people have waitlisted ahead of you and what cancellations occur. Neither of these is really predictable.
2. What do I tell member services when I call? I want to waitlist for a standard view room for my current reservaton + 1 day? What is the least confusing thing for me to say for them and for me.
First, ask if a room is available. You never know.
If not, ask to go on the waitlist. You have two options for waitlisting--the entire trip vs. day by day.
If you do it day-by-day, as each individual day of your stay comes available, you will be moved to the new room category. This has the best chance for success, but there is also risk involved. To be blunt, if you don't get ALL of the days in the Standard View, you'll have to switch rooms (perhaps multiple times) during your stay.
If you waitlist for the entire trip, nothing will happen unless every one of the days on your waitlist comes available at once. If (for example) 5 of 6 days open up, you will still be bypassed on the waitlist and those 5 days will go to another member. This has a lower chance for success, but at least you know you will not have to switch rooms mid-stay.
Regarding the extra day, I don't think you'll even be able to go on the waitlist unless you have the points available to book. If you do a day-by-day waitlist, I'm certain you will have to wait until such time as enough of your points are freed-up to allow you to book the extra day. If you waitlist for the entire stay, they MAY be able to tack on the extra day. If so, just remember that's one more day that needs to be available before you can move.
If you're inclined to waitlist for the entire stay, I'd stick with the dates you have booked now and then try to add the additional day when/if you get the first part of your trip confirmed.
