I must say that I was really impressed with SSR upon my first stay there in September. The grounds are beautiful, transportation was very good, and proximity to DTD is a plus if you spend any time at the shopping village (this would be the same advantage for OKW). Ive never stayed at OKW, so I will refrain from providing my opinions, as anything I have to add would be speculative at best. One factual thing that I can add about OKW is with regard to room size. OKW has the largest Studios of all
DVC resorts, so if your trips are primarily going to be designed around studio accommodations, this might sway you towards OKW.
One other thing that I will mention, some of the best advice around these boards is to Buy where you intend to stay. In other words, if you really enjoy a particular resort and you have to stay there, your best bet is to buy there at make that your home resort, as you are "essentially" guaranteed a room there at the 11 month window. If you do not own at that resort, you are just rolling the dice to get in at the 7 month booking window and may be disappointed at the result. Some people really dont care where they stay, and simply choose to buy where points and/or maintenance fees are lower.
I will say that generally speaking, SSR is the easiest resort to book inside of 7 months due to being the largest DVC resort on property. From what I have seen, it almost always has availability in the 3-5 month window, unless you are talking about peak seasons For this reason, I might steer you towards OKW, as chances are, you can probably book SSR at the 7 month window whenever you want. The only exceptions to this, naturally, would be at peak travel times (i.e. Christmas, Spring Break, etc.).