Stayed at both and each have their pros and their cons.
OKW Pros. If you are planning to spend time together as a group, eating meals in the condo or sitting on your balcony, then you want OKW. OKW has a dining table with chairs and we were able to sit 6 adults easily at the table to play cards, eat, etc. You cannot do that at SSR. Also, the balconies at SSR are much larger; we also sat all 6 of us out there. OKW has a more private feel as the landscaping is fully grown and especially on the balconies, you feel secluded.
OKW Cons. It's older than SSR.
SSR Pros. It's new than OKW and you can walk to DTD if you like a good jaunt. Nicer main pool.
SSR Cons. The 2 bedroom condos are a lot smaller than they were at OKW. As a group of 6 adults we have felt cramped both times we have stayed in a 2 bedroom there.
I have found the bus transportation to be about the same at both resorts (having stayed at each during a slower season and a peak season). Also, both resorts are really spread out and walking from your building to the main pool/lobby/food areas can be a long walk depending on where you are located. Both resorts have boat shuttle to DTD and again, depending on where you are located at the resort, it can be a long walk. I did not find the CM's to be any friendlier at one over the other. They are the same distance from the parks.
Both have main pools and quiet pools. We've used all of them. I would give slight edge to SSR on main pool but not enough that it would determine where I chose to stay.