Well, you can ask...although some will say that it CAN hurt because hotel clerks don't like people always asking for freebies (I know you don't always ask, but think about how many times a day a hotel clerk gets people asking for gimmees...about the 10th person asking would be getting under my skin, lol)
I guess I'd say you can try asking if a better room is available and what would it cost you to move up...if you're lucky, maybe they'd give you the upgrade for free. More likely, if the better room is available, they'll quote you a good price on the upgrade (not free, but cheaper than if you'd booked it that way in the first place.) I've seen that happen...where people ask about an upgrade & got offered the $150 a night upgrade for $50 a night. If you really want an upgrade though, expect to pay for it. And if you're positive you want the better room, book & pay for it in advance because they could sell out before you get there.
We have gotten a couple of minor free upgrades at Disney, and one really nice upgrade...but we didn't ask for them. We just showed up to check in, and there it was...our reservation had been changed to show the upgrade. My understanding from a relative in the hotel business is that generally free upgrades are given for a reason: to reward repeat customers, or to entice repeat customers to move up to more expensive rooms, or to compensate a customer for some inconvenience the hotel has caused (like the room not being ready until long after check-in time because they unexpectedly had to clean the carpet so instead they give you a better room.)
Good Luck
ETA: I see according to your sticker you're staying at POFQ...that's where we got 2 minor free upgrades. Once to a water view, and once to a king-sized bed room. Though nice, those aren't really high-ticket upgrades. The water-view at POFQ is not all that - you don't have a private balcony or patio, so the view doesn't make a whole lot of difference. Have to say, though, there's not a whole lot of difference in the rooms at POFQ- there's no concierge level to upgrade to, and preferred rooms are not really any closer to anything else (it's a small resort! One of the reasons we love it.) And if you were thinking maybe an upgrade to a deluxe resort...that is really extremely RARE. They did some during
free dining from value resorts to SSR and OKW (DVC villa resorts) but that was because they over-sold the value resorts and wanted to free up room inventory at the values. They never moved anyone from the moderates to deluxes. We stayed at POFQ last year during free dining and the place was empty.