You have a few choices when making a reservation through MS that is longer than 7 nights. Your choices for doing this at your home resort are:
1. Call 11 months before check-in date and make the reservation for the first 7 nights; then call each day thereafter until you have your complete desired number of nights.
2. For a 10-night reservation as an example: Call MS 11 months before check-in date and reserve 7 nights. Wait another 3 days to add the remaining 3 nights for a total of 10 nights.
3. For a 10-night reservation as an example: Wait until 3 days after your 11-month window begins. Make the entire 10-night reservation at one time.
I am choosing the first option because I am neurotic when it comes to vacation planning and trying to get what I want, and that option seems the best for me. I'm home for the summer (teacher), so I definitely have the time to call MS at 9AM for a few days in a row. I also do not mind doing this at all, actually it's kind of exciting for me!
Yes, I am an "uber planner" as you said! DH is not into vacation planning, most times it's "Where are we eating tonight and at what time?"!! He leaves it up to me, which I also like. I enjoy doing the planning. However, when we were buying the
DVC membership, we looked at everything together to decide how many points we needed, which home resort we prefer (since we book so far in advance anyway, so home resort was important to us), time of year we prefer to go, etc.
It's nice to know there is a great community here of really terrific people that share the same interests in planning their trips to WDW!