Hi William,
Thanks for visiting the Disney Parks Moms Panel with your excellent question.
Magical room upgrades at the Walt Disney World Resort do happen from time to time. However, they can be few and far between. My family and I have stayed at
Disney Resort Hotels numerous times in all types of room categories, from Standard View Rooms to Club-Level Service Rooms. I can recall one particular instance, at Disney's Yacht Club Resort, when we were upgraded from a Standard View Room-Club Level to a 2-Bedroom Suite with Club Level Access! As you can imagine, it was an extraordinarily pixie-dusted occasion for our entire family and one we will never forget! However, that type of experience is quite an uncommon occurrence.
If your heart is truly set on one particular Disney Resort Hotel, or a specific room type, my recommendation is to book it as soon as possible. Disney Resort Hotels are frequently booked to capacity, and thus upgrades are highly unlikely. That being said, it never hurts to ask nicely. My suggestion is to call Disney a few days prior to arrival, and have them note a room preference on your reservation. You can also fax the request directly to your Disney Resort Hotel. Once on-site, reiterate your desire for an upgrade to see if there is any possibility they can accommodate your request. The absolute worst-case scenario is that they cannot, and then you'll end up staying in the room you originally booked for your vacation.
Wishing your family a most unforgettable visit filled with memories of a lifetime!
Ritzy ºOº