For the ADRs, unless you are booking Xmas or Easter you can also just find a cheap room at the All Stars or wherever and book it for the whole length of your trip, paying the $200 deposit. Cancel with no penalty in a few days as soon as your "second" window is open.
We always do split stay and I have done this multiple times. I never feel bad about it because six months out I'm not hurting anyone by holding that room for a week or so, and it's a workaround for something that you ought to be able to do anyway.