When my Mom & I took a mother-daughter trip six months before my wedding, we paid for a water-view room at POR (then DxL). We wanted a river view, but knew that water view also could mean a view of a pool. So, a few days before we arrived, I faxed the resort. I explained that this was a last, special mother-daughter trip before my wedding, and my mom's first time staying on site (she had previously only been to WDW for a couple of days when my dad had a business trip in Orlando, and they were staying at the Marriott). I made it very clear that I knew they couldn't guarantee a river view, but that I would greatly appreciate anything they could possibly do to make our trip as special as possible. I really tried to emphasize the fact that they would be doing me a huge favor if they could assign us a river view room. I had also requested a particular building - Magnolia Terrace, because we wanted to stay in the Mansions, it had a good location, and it was a nonsmoking building. While this wasn't exactly a request for an upgrade, because we had paid for water view, it was a request for a very particular type of water view room, in a specific building, and they didn't have to honor the request.
Imagine my surprise when my telephone rang at home that night, and it was the room assigner at POR! She just wanted to tell me that she really enjoyed my letter, and that she was assigning us a very nice room with a river view. She warned us that it may not be ready when we arrived, but if we didn't mind waiting until later in the day/evening for our room, it would be ready. She also mentioned that sghe didn't usually do this, but she liked what I had said in my letter about this being our last mother-daughter trip before my wedding.
When we checked in a few days later, we were told by the CM at the desk that the room we had been assigned wasn't ready, so we could either take a different room, or wait for ours to be ready. We said we would gladly wait. We got our room keys & passes, and headed off to Epcot for the afternoon. When we returned to the resort that evening, we called the front desk to verify that our room was ready, and it was, so we went on in. It turned out to be a river view, corner room on the second floor of Magnolia Terrace. Nice view of the river, and the benefit of a corner view room was that we had two windows instead of just one.
I've been rambling, but the point of all this is that they way you ask is very important. It's great if you have a special event or reason behind the trip - birthday, anniversary, etc. Also, be humble. Always emphasize that you know they may not be able to help you, but anything they could do would be greatly appreciated - as someone else mentioned, people are more likely to give you what you want if you don't act like you expect it, or like they have to. I think if you can make the CM feel they they would be doing you a huge favor, and really making your trip fantastic, they are more likely to see what they can do for you.
It wasn't a busy time of year, though.
