We go to WDW every T-giving (we love it)...
1. Last year was our first as
DVC members...we bought June 19; I called MS for T-giving reservations 6/20 (five months out)...had to use the W/L...all but Wed-Thurs (the day before and T-giving itself) were available right away...what I did was probably more complicated (new owner!) than it needed to be...but it all worked out. What I wanted was a studio at SSR for Tues before T-giving til Monday after...I took the Fri-Mon reservation (studio at SSR right away), and then I W/L'ed for any studio or any 1-BR at any resort for Tues-Fri...figured we'd be ok moving if we had to...I wound up clearing the W/L a couple of times (got a 1-BR before I got the studio), but wound up w/exactly what we wanted, by mid-August...I also made a cash reservation at the ASMu as "back up"...once my W/L came thru, I canceled that reservation...
2. I also made our T-giving dinner reservations right away (but it was still way less than 180 days out...about 4 1/2 months out is when I called for dinner reservations)...we got CA Grill (and had lots of choices, since we weren't at all "picky" about time)...then, in October, 4 people joined our party (staying at ASMu) and I had to expand our dinner reservation from 2 to 6...plus, one of the now-six person party didn't have park tix...our choices were VERY limited...we wound up choosing Shula's Steak House at the Swan, where they assured me they'd be serving a traditional Tgiving dinner. When we got there, they only had their regular menu (principally steaks)...my family was thrilled (the food was excellent), but I was disappointed...I really wanted my roast turkey & stuffing and sweet potatoes! But when I got back to SSR, I discovered that Artist's Palette was serving a lovely traditional roast turkey dinner (real turkey, not that pressed kind)! So I got my traditional dinner and I was a happy camper. Moral of the story: even if you wind up having to use a food court/counter service type place, the T-giving meal is very good...
3. Crowds. Yup, it's very crowded T-giving week...especially Wed-Sun afternoon...but it's manageable if you get to your park of choice early (opening or close to it), make use of fast passes, and plan to leave (or don't mind very crowded walking around) by lunch time...night time at Epcot was wonderful, and we saw Fantasmic (at MGM) on T-giving night and it was, well, fantasmic! It was a last minute decision...finished at Shula's around 6:15 and "beat feet" over to MGM...got seats and everything (altho it was indeed crowded)...it was after Fantasmic and returning to SSR that I discovered my "real" (and second) T-giving meal!
SSR was phenomenal at T-giving...sold out but didn't give any "feel" of being crowded or busy at all...and being able to stroll over to DTD at night was great...especially since DTD was uncomfortably crowded...it was nice to "get the taste" of it we were looking for, and then have very easy access back "home" when the crowds got to be too much for us...
SSR was also wonderful for accessing my family at ASMu and the restaurants at the BC/YC/BW (we ate at Beaches 'n Cream, Cape May & Shula's)...just a lovely five-minute stroll (we were in Congress Park) over to the MarketPlace bus stop where we could get the resort busses, instead of having to bus to Epcot or MGM and walk over...
In short, we loved it...of course, we were back in Janary (we arrived in time for the marathon--which was awesome to watch! and stayed a week) and the much lighter crowds were wondrous! But the holiday decorations during the T-giving trip were also awesome...so, we loved both trips...for different reasons and at different paces.
Hope this helps you decide...and that you love it as much as we did...