Thank you for your advice! I think i put it to good use!
I thought I would just update what I did and what has happened...just for the next person who is wondering about this time of year.
I had these reservations on points:
Nov 18-22 at OKW in a 1 BR (NOT HH)
Nothing was available at OKW after that.
I booked Nov 22 for 1 night in a 1BR at SS.
I waitlisted Nov 22-26 at OKW for both a 1 BR and a 2 BR.
THEN..after reading the above advice:
I called MS and booked a cash reservation for Nov 22-26 OKW 1 BR.
LAST NIGHT night, I randomly got on and saw that Nov 21 -25 was available at OKW 1 BR Near HH(none of those dates were available the day before).....SO...
I booked that on points!
I cancelled the SS
I changed my WL to Nov 18-21 1BR OKW near HH and
WL Nov 25th 1 BR near HH
TODAY...I called MS and asked them to put in a request on my CASH reservation to be near the HH and cancelled Nov 21 (NON HH), since I had gotten that date on the HH reservation.
I didn't cancel any part of the cash reservation yet, but my hope is I will only need 1 night at most.
MS was very helpful. Interesting comment though: She told me that when she went in to change my first resize, the computer told her I was double booked (because I had a $ and a points resize for the same dates) and wanted to cancel one of them. Because I had told her that I was trying to piece together this trip, she overrode it.....by changing the $ resize to my husband's name. She told me it happens a lot and if you have two reservations for the same dates (for friends, whatever) to make the primary different on each one. Then it won't cancel. This might be widely known....but i thought I would mention in case there are others out there like me, who didn't know!
So....I got Thanksgiving night and the day before, which were my big worry! Yay! And...worse case scenario is we have to move!
Thanks again to those who offered helpful advice. I so love knowing there is so much expertise on these boards.