Triple amazing news:
My cousin is coming to visit from Italy for three weeks in January. We're going to Hawaii. And I found a super-mega good deal on Expedia!!!!

Before I booked the package, I called the Sheraton to try to weasel out some sort of extra-special deal. I explained that I'm coming to Kauai for the first time and selecting between several hotels. Theirs looks lovely, but I'm still looking at a few options. Is there any chance they'd be willing to throw in a free car rental, to help seal the deal?
"We do have a free car option! What nights would you be coming? I can make the reservation right now. That rate comes out to... let me see... $368."
Cough. I explained that I'm going to book it through Expedia, and she replied that the car promo doesn't work with any other reservation but theirs.
Next, I tried for a luau.

By now, after 150+ days of asking, I really am shameless. Not terribly successful, it seems, but at least the anxiety of asking has long subsided.
She friendly-ly declined, but said they'll do everything they can to make my stay as nice as possible.
I didn't wait much after I hung up to reserve the package. Five nights, including air, at the Sheraton Kauai, which has a poolside bar -- crucial! $750. 24 hour sale. Couldn't pass that up, luau be damned.
Gained: Nothing. But, I will definitely see if I can score some deals once I'm there, and stretch these grad student dollars...