I haven't tried OKW. BUT I love SSR.
Artists Pallet is my fav place to have morning coffee/breakfast of all resorts I have stayed at. (BC, AK, POR, FQ, BWV, ASM, POP)
Being able to drink your coffee, while your kid is entertained (coloring) and having an atmosphere you never grow tired of seeing is fantastic. The art is everywhere, and I believe you would have a hard time every seeing it all.
Also the THV for the same points as a 2 bedroom is a freebee bonus. I believe one day (when fully sold out) it will cost more for those, but for now that is an added bonus. No other resort has anything like this. Taking a second family and allowing the kids to all have their own room.
For the price diff, you get extra years for nearly the same $$. Last checked resale they were about 5-10$ difference.
THE pools at SSR are second only to the BC, and I cannot wait to see the new pad pool/splash area. Walking to dinner at DTD after resting for a few after a park day is the ending to a perfect day.
I have tried booking OKW 2 times to save on a few points, both times I immediate called and went back to SSR.

I think I am just in love.