I have found , pretty much universally, that the "official" upgrade policy is often never followed at resort hotels. For the most part, if resorts give you an upgrade, it is often a "one class" upgrade, no matter how many empty rooms they have, excluding suites.

It is harder for the front desk at resorts to respond honestly when you have your mobile ap open showing how many better rooms they are actually selling when you check-in, but resort front desks seem to give you the hardest time. Particularly if you have Gold status.