We generally go with whatever is available and most cost-effective at the time. But not always. We love OKW because of the extra roominess, but we own at SSR so when we want to book far-out, then we'll book there (and check later on to change if we need to - we just did this for our stay at the Boardwalk in October - we had SSR but wanted Boardwalk because DH will be doing the Race for the Taste -- so we got SSR because we wanted to be guaranteed of a place to stay and then booked Boardwalk when we were within the 7-month window and then cancelled SSR).
We're staying at Beach Club next weekend because we've never stayed there and thought we'd like to try it out -- not cost-effective for us point-wise as it's a weekend, but it is the end-of-school trip and the kids have been wanting to try out Stormalong Bay.
We like Wilderness Lodge Villas around the winter holidays.
With Boardwalk and Beach Club stays upcoming, we'll have stayed at the main five plus Vero Beach. We hope to get in at Hilton Head for some days in March/April '09, and of course we'd love to stay at AKV to try them out - but probably for a trip where we aren't planning to go to the parks.