We love both OKW and SSR...here's some pro's and con's for both:
1. The SSR studio is smaller, but not so much smaller that it would make any difference to me...
2. As you noted, the OKW studio has two beds, while the SSR studio has one bed and a (comfortable) sleeper sofa
3. You can walk from OKW to Downtown Disney, but it's about a mile from the entry point to OKW (South Point) -- and longer from other parts of OKW...Downtown Disney is an easy walk from SSR
4. In our experience, bus service from both SSR and OKW are about equal...both have 5 internal bus stops and they're within spittin' distance of the same length of trip to all the parks. We've never had anything but good-to-stellar bus service at both resorts.
5. Counter service eating is better (we think) at SSR...the only quick serve option at OKW is an outside food stand--the food is good, but there's no inside seating area and the choices are limited. SSR choices aren't all that extensive, either--but there's more choice at Artist Palette than at OKW's quick service spot.
6. OKW pools are great, but SSR's are a tad better...the view of Downtown Disney from the Congress Park quiet pool is spectacular, and the feature pool at SSR is terrific...so, too, is the Grandstand pool--which is a bit better (water play area) than a quiet pool, but not quite a feature pool (no slide)
7. Both resorts are wonderful for strolling (or exercise--jogging or hiking)...both are very, very pretty and have extensive 'walkways'...
8. We love both table service restaurants (Olivia's at OKW and Turf Club at SSR)...definitely a coin toss between the two, altho they're quite different...
For us, it's really a coin toss between the two resorts...the themes are very different, but the features and feel are very similar...but OKW takes lots fewer points...for our last minute trips, often they are the only two resorts w/availability and we switch back and forth -- I prefer to stay at a different resort every trip, and certainly to not stay in the same resort for two trips in a row (altho that has happened)...so, if we haven't "just" stayed at either, we'd pick OKW just for the fewer points required...
As for requesting a particular area: if you think you'll want to walk to Downtown Disney, you might want to ask for Southpoint...it'll shave 1/4 mile (or more) off the walk...I presume "near Hospitality House" isn't available, as it is a separate booking category--but if you can get that, it's the closest to the main pool/food/store/check-in. My personal non-HH category area is Turtle Pond...but that may be emotional more than anything else. I like the quiet pool in the Turtle Pond "neighborhood" and it was the first place we stayed at OKW and I have very fond memories of it! No "neighborhood" is more than a 10-minute (or so) walk from the main area (pool, restaurants, store, community hall), and you can hop on any bus to get over to the Hospitality House, too...
