Those are all great resorts!
No question, I would do the two bedroom unit at OKW. Simply for the square footage, you have a big group. The fact you are getting such a great deal seals the deal. And because you are cash, you will get daily maid service at both SSR and OKW (
DVC members staying on points do not get daily maid service).
At OKW your unit will be huge at 1395 square feet. At SSR, the two bedrooms are around 1070 square feet.
At CBR, you'll get two rooms that are around 340 square feet each.
In a two bedroom you'll have a King in the master, a jucuzzi tub in the master, a balcony (and the balconies at OKW are huge, more like porches with tables that seat four, and a ceiling fan, at SSR balconies seat two, no celing fan on those). You'll have a full kitchen and the laundry. At OKW the laundry is in a separate, nice sized laundry room with a full size washer and dryer. At ssr, its a stackable in a closet.
I love all these resorts, but having a two bedroom unit will give you a lot of space, a balcony and a lot more total square footage. Also, both of those resorts are close to DTD which is a nice perk.
You asked about the Pirate rooms at CBR, those are the furthest out, however the walk is roughly 8-10 minutes to the main area and you have a quiet pool and bus stop right there in your village.
The best pool scene of the three is probably SSR's, High Rock Springs pool is amazing, they have a second feature pool in the Grandstand and another main pool being built in the Paddock area (not sure when that will be done). CBR's pool is great, but I think its best for kids 12 and under. My two teenagers were sort of bummed with that pool, it was always packed with little kids and some areas are gated off for older kids. Which is great if you have little kids of course!
OKW also has a really nice pool, my kids love the sand castle slide.
I'll also add that both SSR and OKW have community halls with ping pong, air hockey, games, pool games, SSR has crafts and classes offered (for a small fee, I think I paid $3 each for my kids to make ice cream one time and they had a ball), poolside games and contests and movies shown several nights a week on a big inflatable screen.
You'll also have a DVD Player in the living room of either SSR or OKW and they have free movie rentals at the gift shop at SSR and at Community Hall at OKW.
All three resorts are spread out, and you can have as much a ten minute walk to the main area at any of them if you get a building that is removed. CBR is the only one where you can book an actual preferred location (between 25-30 per night extra) that guarantees you a close in spot. All three of them do have quiet pools (or a main pool) near each section and a bus stop in each section.
Hope that helps!