Update: We've given up on the Grand Wailea. I've called a couple more travel agencies, and they are all quoting $400/night+ for the lowest-quality room in the hotel. I'm sure it's a nice place, but I can't justify that kind of coin, especially knowing that free upgrades are pretty much impossible to get.

Instead, we're doing an award stay at the Renaissance. We'll have a beachfront room in a semi-private wing of the hotel. Looks very nice, and it's only a 15 minute walk down to the Grand Wailea if we want to go to their spa.