OKW is my favorite resort. Since we visit in summer due to school schedule we go in June and Aug every year. I've tried to get THV for June several times at the 7 month mark but have yet to be successful.
OKW/SSR are both near our favorite water park, Typhoon Lagoon, it's so much fun and cool(love the wave pool). We really enjoy Downtown Disney, we go to the movies there too. You can walk there from SSR/OKW or better yet take the boat to and from, at night it's really beautiful. My son loves tennis and I love to walk so OKW fits us quite well! We bicycle, June is still a bit less humid and hot than Jul, Aug, & Sep. This year we went to FW, the boys love to fish and they also did archery. There's really a lot to do in that area.
We drive in so having a car let's you experience other things non-Disney. I never get to shop other then when on vacation, so we hit the outlet mall, just a right at Crossroads intersection and head to Vineland. Great way to spend an afternoon! We also like to eat outside of Disney as well, Timpanos Italian Chop House is one of our favorites.
As far as Disney dining, we love Olivia's/OKW, Turf Club/SSR, Wolfgang Pucks Cafe/T-Rex/DTD. We are hoping that the new Pollo Campero is open in DTD this Nov, it's replacing the Macdonalds that was there.
As Floridian's we've gone to Disney so many times that now the resort and it's surrounding are just as important if not more so than the theme parks!