Resort preferences are very personal. For that reason, my advise is to try each resort at least once during the ownership of your DVC membership. Then you'll know which ones you like and which ones you don't. For ourselves, we found that doing split stays helped us to explore and try all the resort more quickly. If we're down for a quick stay of a long weekend or less than a week, certainly we'll stay in the same room. But our summer trips that last two weeks are always split between at least two different resorts. (It makes it seem like two different vacations.)
SSR happens to be my most favorite resort, although I thoroughly enjoy our other two home resorts as well. I make sure we spend at least one week at SSR every year. I love the look, feel, and theming of the whole resort; like the way that transportation is consistent to every park; find it to be one of the most convenient resorts when we have a rental car; like that we're close to both Downtown Disney and the Crossroads Shopping Center (where we have quite a few favorite restaurants); love the pools; find the dining options to have some of the best selection of the various DVC resorts; and find that it's the resort where we somehow have the most-relaxed, laid back vacations.
To prove how subjective resort preferences are, SSR is my favorite and OKW is one of my least favorite. The resorts are similiar in many ways, so you might think I'd like them about the same. Nope. The only one I liked less than OKW was AKV. (That's all relative, though. Every single WDW DVC resort is wonderful in its own way, and I wouldn't hesitate to stay at any of them again. Given the choice, though, OKW and AKV would be at the very bottom of my booking priority.)
It's difficult to put a finger on why OKW didn't click for me. A few of the things I listed for SSR apply to OKW, too. Some of the things I didn't like at OKW were the decor of the rooms, the overall layout of the resort, the counter service dining option, and the pool. I also wasn't thrilled at carrying luggage and groceries up steps.
There are owner/lover threads for both resorts. You may want to take a look through these. They may give you a few ideas.
SSR OKW