Love both, but very different. As other posters have said, OKW has large, lovely units with big balconies and lush beautiful landscaping. DH and I love having a delicious meal at Olivia's while the kiddies play at the pool. The Gurgling suitcase bar and pool area is very family friendly. Its also beautiful at night. I think my mom would def vote for OKW and the pool area. The quiet pools are small, but very nice. Very few elevators to the upper units! The way the hospitality house, etc is lit up at night against the water is gorgeous.
SSR is new and under construction, so to us it still feels a bit new and bare. The sit down restaurant doesn't compare to Olivia's, but supposedly a new resaturant is on the way. The units are smaller, but very lovely and elegant - like a country club atmosphere. Maybe bcs it was new and bare, it doesn't seem as many people are there helping like OKW. It doesn't yet have the community feel that OKW has - but give it time. The pool is fine, as is the pool bar. The quiet pool that looks out over DD is GORGEOUS, and if you can get a down town disney view, its great. We loved the turf club and country club feel, and immature magnolias. Maybe appealed to the snobs in us! Elevators to all the units. The spa was wonderful.
Frankly, I think SSR will be gorgeous once it gets going and works out some kinks and is fine now, but we love love the tropical feel and community atmosphere OKW has (esp. coming from Minnesota!) By the way OKW is kept up very well.
I think anywhere you stay will be wonderful. Once you stay at a few, you will see its really personal preferences and comparing apples to oranges!