OKW has always been our favourite - but SSR has good points too.
OKW was built before Disney figured out how to downsize. The size of the suites are in a class of their own. While you always get the feeling that the other DVCs are “vacation” villas, OKW gives you the feeling that you could move right in and stay forever. They just seem more condo-like. Many say that OKW doesn’t have the same “Disney” feel, but I disagree. Just dealing with the very best CMs at WDW makes it feel very Disney. Olivia’s is one of the best sleeper restaurants at WDW. The store is well-stocked with groceries you might have forgotten. The grounds are beautiful. On the “downside” - the place is enormous, but so is SSR. There is no counterservice restaurant. Some complain about the bus service, but we’ve never had a problem. OKW has a very private “exclusive-club” feel. As the oldest DVC many have been coming here for years and have sort of made it their own. Some like that, some don’t.
SSR is a beautiful resort too, but the suites and veranda/balconies are half the size of OKW. Not that they are “small” - just small when compared to OKW. The grounds are beautiful, but huge. The store/counterservice restaurant area was not well-thought-out. It can get really badly congested when people are ordering their food and waiting around for it. The Artist’s Palette dining area isn’t very Disney - it almost seems like an afterthought they stuck in, so people wouldn’t complain there wasn’t a counterservice. The Turf Club, though, is another terrific restaurant. One of the best with really nice servers. With the addition of the new pool in the Paddock area, SSR now has two “main” type pools, with slides. People here also complain about the bus service - but people complain about the bus service no matter where you are in WDW. It’s location is wonderful, right next to the Marketplace and you can walk there or take the boat. Of course, it has a wonderful spa too. It has a more “vacationy” casual feel to it, which is very nice and relaxing.
A plus for both is if you have a car. You can park right outside your suite which is very convenient.
It’s hard to say…there are pluses and minuses to each. I’d stay at either, happily, but if pushed…OKW would be my first choice.