Upgrades are generally assigned in advance by the resort, due to their own operational needs. It's just a matter of being in the right place at the right time, and it happens a lot less frequently than you would think by reading these boards. Rule one of message boards....just because people talk about something a lot, doesn't mean it happens a lot.

Asking for a free upgrade at check-in is not recommended. Resorts don't hand out upgrades they can charge for just for the asking, and it puts the CM in an uncomfortable position. In fact, multiple CMs have posted here that the best way to ensure that you won't get a complimentary upgrade.....is to ask for one. On the rare occasion that they do have the ability to do an upgrade, they'd much rather surprise a guest with one ("pixie dust"), than just give it to someone who walks up and asks for a freebie. If you really, really, really want the preferred room at Pop, the best way to get it is to call and change your reservation. Or, you can ask what the upgrade would cost at check-in.