I actually had 2 positive experiences last November getting upgraded in Maui and Kauai. I am a Starwood Gold.

Mrs. cantstop & I were upgraded at the Sheraton Maui resort from a cheap run of the resort room booking to an oceanfront. We were also given a late checkout with no hassle.

The Princeville Resort was an award stay and we were given a much nicer bayfront room than in 2003 (when I had no status). Getting them to give me a late checkout was a little hassle though. I wished to leave at 4pm and the latest they would allow was 2 pm. It was a Saturday, so we did a little extra sightseeing before our flight home.