I was on that linked "heated" thread (and have sinced pm'd and gotten on very nicely with the other poster I might add) and just have to say this. If you realize that these resorts are:
Not really hotels in the usual sense of the word, but rather more condo like, with lots of buildings, spread out, and don't offer things like room service, typical deluxe amenities like bathrobes in the room and daily maid service (if you are staying on points) then I think either resort is wonderful.
We just got back from OKW and loved it. SSR is my home resort but I now typically just take turns between it and OKW.
The OKW units are more spacious, you will get a huge balcony/porch type thing in the one and two bedrooms. A full size washer and dryer and just a ton of space.
The SSR units are not quite as spacious, however I have stayed in two, two bedrooms with family members (six total) and they are lovely. Not as spacious but newer, more elegant furnishings, but smaller balconies for sure. And a much smaller kitchen. Stackable washer and dryer in a closet vs. a full size in a small laundry room.
OKW has tropical theming, palm trees, a tropical themed pool and two cs options. When we were there last week, there was Olivia's of course then there was Goods to Go which has limited offerings (burger, hot dog, chicken strips, chicken caesar salad, tuna sandwich, pretzels, onion rings, and I think a turkey wrap or sandwich). there is the Gurgling Suitcase that has a full bar. Then there was the Turtle Shack which had some snacky type things and I believe hot dogs. As well as beer, smoothies and a soda refill station.
SSR has Artist's Palette which I think is great cs. Flatbread pizzas, sandwiches, salads, chicken strips, hot dogs and a bakery.
SSR has Turf Club, OKW has Olivia's for full service. We ate at both of those during this most recent trip and enjoyed our meals at both.
Both resorts have small stores, but SSR's seems bigger.
As far as pools, SSR being newer has a more state of the art pool area with zero entry, spray jets for the kids, a large slide and a small slide (OKW's pool only has the larger slide). At SSR's pool they often play games with the kids I haven't seen that ever at OKW. SSR also has a second themed pool in the Grandstand area with spray cannons and a separate pool bar and drink station (sort of like the Turtle Pond pool with the Turtle Shack at OK).
If you go with OKW, its nice that you can now gurantee being near the main area if its available. If you go with SSR, I prefer the Grandstand over the Springs. The Grandstand is very close to the springs however, its the first to be picked up and dropped off on the bus route. The Springs is last. So if you are planning on bussing, I would try for the Grandstand. The busses can sometimes be crowded by the time they reach the Springs section. We also love the Paddock area, nice and quiet, I believe second or third on the bus route and very peaceful. And an easy, short walk to the main area across a bridge.
I love both resorts equally. SSR being newer needs some time for its landscaping to mature a bit (although I think the grounds are beautiful, just not as lush as OKW's). But to me its being new is also a huge plus, the units are so fresh and clean. The whole resort is immaculate. OKW is also lovely but I have to say, our recent unit was a tiny bit worn in places (not dirty at all, just some frayed carpet, one slat on the blinds was broken, its not brand new so you have to expect that sort of thing, again, it was spotless). And just little things like the light fixture outside our door was dirty and full of dead bugs. For some reason that sort of bothered me. But the unit was still spotlessly clean inside and I love the furnishings. SSR feels more formal. OKW is definitely older, but the plus to that is that the landscaping is mature and the units are more spacious. And at OKW the second bedroom will always have two beds, vs. the possiblity of getting a lockoff at SSR with a room that has a bed and sofa bed. OKW is so laid back, it feels very cozy and friendly. A lot of the cm's seemed to have worked there a long time and know some of the long time guests. It truly feels like a community of friends. SSR cm's have always been great for us too, but it doesn't have quite the same homey feel. Its not as laid back and it doesn't feel as themed. At OKW you'd swear you were in Old Key West, at SSR, the race horse theming is more subtle in a sense and a lot of people find it lacking in overall theming.
Both resorts have great access by boat to DTD. OKW has a walking path somewhere that closes at dark, SSR is an easy walk from the Congress Park area at anytime of day or night. Some of the units at SSR has nice views of DTD and the Cirque tent.
And of course be aware (this may have been mentioned) that on points, you won't get daily maid service. If you want that, you have to pay extra and arrange that ahead of time. You do get trash and towel service on day 4, if you are staying longer than a week, you will get full maid service. For our recent fifteen nights, we got full service twice, and trash and towel once. Each unit (in both resorts) has a vacum cleaner if you need to do a bit of cleaning up yourself!
If you haven't already, go over to
www.allearsnet.com and check out the slide shows for both resorts.
I don't think you can make a bad choice!
If your uncle has some points for you to buy (at what I assume might be a nice family discount!) I'd jump on that. Dh and I really want to buy an OKW contract at some point so that we have contracts at both SSR and OKW. OKW is the only resort besides SSR I'd want to buy at, we absolutely love it. If you stay there before you buy, I am betting you'll buy afterwards! If you stay after you buy his points, I promise you won't regret it.
OKW was the first 
Taking a boat over to DTD is one of our favorite things to do. 
I'm not familiar with OKW (never stayed there), but he said it's a great resort that's more "condo" like with large rooms and parking available just outside your door. I'm interested in hearing more about this 
