During busy times, it doesn't matter...if they have most of the rooms sold, they won't offer. If it is during a "non-peak" time, you are more likely to get upgraded. It just depends on the resort and time of year!
The room assigner has already assigned you to a room before your check in day. I think if you check in early you have a better chance of changing something assigned to you ~ before others have shown up and asked for changes or possible upgrades. Of course during peak season it will be difficult if not impossible to be upgraded, since the resorts are booked and the better view rooms are paid for by someone already. They can only upgrade you when the resorts are not full.
The past 3 times we've been to DW we checked in before 11am. When we arrived to check in, I asked if I had a choice of locations and they asked what I would like. All 3 times we got exactly what we wanted. Two of the 3 times we had to wait to get the room, but that didn't matter, we just headed to a park. When we got back a few hours later the room was ready. Maybe we were just lucky, but I do think it helps...
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