We've received free upgrades both at GCH and DLH, but that was pre-Covid. Who knows, now? With GCH, I called ahead and talked to reservations to request an area of the hotel (near the elevators) and asked politely if there might be a possibility of a free upgrade. They upgraded us to a wonderful room facing the courtyard with the monorail running through, and we could see the high fireworks over the roof opposite. That was several years ago. I would advise calling ahead to talk to room reservations if you can, but from what I am hearing, the wait on hold lately is abominable. It might be really hard to get through. In 2019 at DLH I asked at check-in and received a pool view in the Adventure tower.
Here's the thing. My kids and husband slightly cringe to hear/watch me do this; they get kind of embarrassed because they think I'm gushing and I'm not normally a gushing sort of person, though I'm cheerful and pleasant (gotta be, I'm a kid's librarian!). But I'm not ashamed to slightly gush when I'm asking for an upgrade. At DLH two years ago, I was checking in with receptionist, and by golly, I leaned on that counter and told her with a big smile how excited I was, because it was my birthday trip, and the whole family was back for the first time in 11 years, including my daughter and son-in-law! We had reservations for lunch at Club 33 (thanks to DH's work), and Napa Rose chef's counter another day, and she heard ALLLL about it. I had her gushing right along with me. I asked politely and oh, so sweetly if there was any possibility of getting DD and DSIL on the same floor with us, and maybe an upgrade to a higher floor? By this time, she was busily typing with a big smile on her face, and said, "Oh, yeah. We're going to make the magic happen." We got connecting rooms for the younger 2 DDs and DH and I, overlooking the pool, I think it was just 4th floor, but good... DD and DSIL were just further along the hall. It was pretty sweet. So... don't be hesitant to be cheerful and polite. It often pays off big in pixie dust!