We're headed back to WBC on August 5th for our second visit (first was October 2011), staying in a 2BR presidential. We're Wyndham owners, but are stockpiling all our points for a pull-out-the-stops trip to Hawaii next year, so wound up renting the week for $1385 from denisetravels. Here are some tips I thought might be helpful:
Internet (if you find the new all-over wifi insufficient): for one laptop, there's a cable provided, hanging off the back of the kitchen phone, you can just plug in (computer-->phone-->wall). When I tried this last year with a router, the phone kept rebooting and kicking us off, so I wound up just unplugging the phone and plugging the router directly into the wall jack. Worked a treat the whole trip.
Arrival/Shopping: What we usually do (did 2 weeks ago in Vegas, and are doing in 2 weeks in Orlando), is to take an early flight in. We get in at 10:45, will grab our luggage and the car, and head to lunch. After lunch, stop by the resort, do the pre-check-in dance (so they'll call us when our room is ready) and leave our luggage with the bellman. Around 2pm, we'll head out to a grocery store to stock up for the week. We liked the Winn-Dixie last year because of the great employees--one literally chased us out into the parking lot to give my son (4 at the time) a sheet of stickers. By the time we're heading back with our haul, the resort will be calling us to say our room's ready, and we can go right up. When we get there, we call the bellman and our luggage gets delivered while we load the fridge/cabinets. So we're in the room and unpacked at the same time we would have been had we not made the trip, but now we're loaded for the week.
Packing: pack LIGHT! The two best things about staying in a condo instead of a hotel are the space, and the washer/dryer. As a result, you don't have to bring 100lbs of luggage per person. When we were in Vegas for two weeks, we checked 1 rollaboard, one small suitcase, and one large suitcase for 4 people, total of around 120lbs including the bags themselves (call it 80lbs of our stuff). We're all in agreement that even that little bit was too much. For me it's 3 pair of shorts/shirts/underwear/socks, a pair of water shoes, 2 swimsuits and a shirt to wear to the pool, plus some minor toiletries and a roku 2. Doing a load or two of laundry per day is maybe 8 minutes total work, and easily offsets the need to lug 10-15 sets of clothes per person. We never stay in hotels anymore except for 1-2 night trips for this reason alone. They don't give you much detergent though, and I don't trust what they do provide, so we bring an old shampoo bottle filled with the Costco environmentally-friendly detergent (which we like not for the obvious reason, but because the coconut/palm oil base doesn't irritate my wife's skin like many chemical ones do), use liberally throughout the trip, and then discard before we leave.
Carseats/strollers: bring your own. It saves money, they're more comfortable because your kids are used to them, and it's very easy. Travel bags for each are available cheaply--if you're bringing a second-stage booster you don't even need a bag--and the airlines can't charge you for them. Check the carseat in its bag at the curb. You can even stuff some extra stuff in there--I usually put my pillow in. Doesn't count as a bag, so you won't be charged. Then we let my son ride in the stroller through the airport, fold it up put it in the bag and gate check it. It's waiting for us as soon as we get off the plane, and he can ride it back out of the airport. Works like a champ. And then when we get in the car, it's not the luck of the draw (which we always lose) with regards to how uncomfortable he's going to be. One one trip, he was the ONLY one that was comfortable in the terrible Grand Marquis we got stuck with.
More to follow, I have to head home now...