We've stayed at both OKW and SSR with 3 kids (using a double stroller and a single stroller, too!).
Both have pros, so it all depends on what's important to you.
OKW pros:
- larger rooms
- patios and balconies are larger and even the first floor ones have a railing around them to keep little ones from wandering off into the shrubbery. LOVE being able to leave the door ajar and let them wander in/out. SSR 1st floor patios have no barrier.
- little ones can stand on the tiled step next to the bathtub and access the bathroom sink for hand washing, teeth brushing, etc. There is no way, aside from using a kitchen chair or sitting on mom's knee

that the little ones (approx 3 yrs and under) can reach the bathroom sink(s) on their own at SSR. This may be a minor point but for us it became quite the inconvenience at SSR until we went to
Walmart and bought a stepstool.
SSR pros:
- zero entry pool is simply awesome
- walking distance to Downtown Disney. Yes, you can walk/bike from OKW but it's quite a bit farther.
- crayons and paper at the Artist's Palette restaurant. Kids loved that little touch!
Both are great for leisurely walks with the strollers, sightseeing, etc. We never used the buses as it's a pain with the strollers and in all honesty takes longer to wait for the bus, collapse strollers (while one parent tries to keep 3 pint-sized tornadoes within arm's reach), get on bus, get off bus and deal with strollers again than it does to just leisurely walk to anyplace on the resort.
Overall, I think OKW has better ROOM-BASED amenities, while SSR has better OUTSIDE the room amenities. Having stayed at both, we now prefer SSR because of the proximity to DTD and the pool. And we keep a folding stepstool for the kids to use at the bathroom sink in our Owner's Locker...
