We have stayed at both, and much prefer OKW, but then it is our "home". SSR (Saratoga, not Sarasota) is nice and new, quiet, HUGE and has nice amenities, but we much prefer the less formal, more laid back atmosphere at OKW, and LOVE the "vacation home" feel there that is just more private feeling. We also love the larger rooms at OKW, and the much better kitchen/living room area and large balcony. Views are lots better at OKW too unless you happen to get a DTD view at SSR. Just more good views at OKW. SSR has more upscale feeling furnishings, but it feels "stuffy" to me. YOu may feel otherwise.
BTW, you can walk to DTD from BOTH resorts, and OKW will not necessarily be a longer walk that SSR depending on where in each resort you are staying.
Olivia's is a great place for a casual meal, but SSR's Turf club has good food too. Again, it seems more formal than Olivia's.