So far, every
DVC resort I've visited has had something I really liked about it---and a few things I didn't.
SSR and OKW have two important things in common. First, they are genuine respites from the theme parks. There are a few others that manage this, but most do not. Second, they do not hit you over the head with
Hey, You Are At Walt Disney World! everywhere you turn. For many, these two are negatives, but for me they are positives.
Transportation is surprisingly efficient. They both have reasonably central locations and are close to high-volume arteries, and there aren't many other resorts that are so located. This tends to counter-balance the internal bus loops. I find OKW's internal loop a little more annoying because of all of the turnarounds vs. SSR's which is more or less just one big loop. But, if you are staying anywhere near the Hospitality House, on the "top half" of Miller's Road, or anywhere on Peninsular Road, you can get off at Peninsular (the first stop) and on at Hospitality (the last one). The last time I was there, in early spring of this year, they also sometimes ran split routes in the morning to MK, which also sped things up.
Between the two, there are also some important differences. OKW is more casual, and it constantly whispers "relax, you're on island time". The landscaping is lush. Olivia's is one of my short-list of restaurants for any trip. The food varies from year to year from "only okay" to "pretty darn good" but they nail the cozy welcoming vibe better than almost anywhere else on property. The boat ride to Disney Springs is one of this resort's highlights for an evening out.
In contrast, I'd describe SSR as quietly sophisticated---particularly so after the to-the-studs refurbishment a few years ago. As noted, the walking paths in SSR are lovely. They are on the "interior" of the resort, away from the roadways, which I enjoy more than OKW's layout. SSR's counter service options are vastly superior to OKW's (not a high bar; Goods to Go is pretty much at the bottom of the list). Having Disney Springs in your backyard provides for a more energetic atmosphere.
I've never stayed in studios at either. However, there is one very important difference: OKW has two real beds, but no couch. SSR has the murphy. I like the latter because it makes the room much more flexible, but if you need both sleeping spaces, you might prefer OKW.
When SSR first came online, I would have told you I preferred OKW. Partly that's because SSR's vibe in the early days was "McMansions on a Moonscape"---the landscaping was very immature in the early days*. But, now that everything has grown in the experience is quite different. Throw in the refurb and I think SSR might nudge OKW overall. But, the "island time" vibe at OKW still holds a lot of appeal to me.
Most owners like to look down their noses at these two. Personally, I think they are missing out on some lovely experiences. I think it is worth trying.
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*: If you remember what "Act One" of Everest looked like when it first opened, think that look but everywhere.
