I used to work at a Disney Deluxe front desk, so here's my $.02.
As others have said, upgrades are only done for operational needs. If someone asked for an upgrade, I would say, "We don't give complementary upgrades. If you'd like, I can ask what the price differential would be per night." 99% of guests would then say "no thanks", but it
always soured the rest of the check in. It made them seem cheap, I
knew that they were paying top dollar for the resort, so obviously they weren't cheap, but it was obvious that they wanted something for nothing, if that makes sense. We never gave a discounted price, it's always full price or nothing. The best way to ask is: How much extra would it cost to upgrade to xx room? Then you're not inferring you want anything free, but you may get some extra magic.
Some resorts do free upgrades. I don't want to name any because it could have changed over the last year. But again, ask as I mentioned above, and the worst they can say is full price, and you have every right to politely decline.
You would laugh at all the silly things guests do for free upgrades! Can't name them on here but I've seen some wild stuff
And saying, "if you want to bump me to the presidential for free, I wouldn't mind!" is not original, we heard that at least once a week
