Both are great resorts for varying reasons:
1. Both are near DS with a nod to SSR for a close boat or walk. But OKW isn't too much farther by boat.
2. Olivias IMO at OKW is a better eatery than The Turf Club at SSR, but SSR QS place is way better than OKW, with better variety.
3. Bus service is about the same at both, with several stops depending upon which part of either resort you are staying in.
4. Pools are great at each
5. Rooms are bigger at OKW. If you are staying in a 1 or 2 bedroom, nod goes to OKW. The size of room will spoil you. But if studios are your preference, I would stay at SSR. OKW studio just feels like a big hotel room, SSR is more like a true studio. Maybe look at room layouts of each if this matters
6. OKW to me seems quite, maybe with less hustle and bustle, and walk to front area not as far as some of the rooms can be at SSR. We like Turtle Pond area at OKW, Grandstand at SSR
7. If you want a nightcap, Gurgling Suitcase at OKW is small but can be busy. Turf Club Bar at SSR has smaller selections but more room to sit, and tends to be far less crowded
I know this is a lot of info but maybe it can help to weigh out likes/dislikes and go from there.