Hi Stephanie!
Disney's Online Resort Check-In is a great way to streamline your check-in process, that way you can get to the fun more quickly! Upon arrival you will just need to show a photo id, your welcome packet and Key To The World Cards (if not using Magic Bands) will be waiting. Rooms are not assigned well in advance, due to cancellations and other issues a cast member will typically wait until shortly before you trip to schedule room assignments. If you need your room ready earlier than the standard check-in time, make sure to check the box indicating this when making room requests during your online check-in. This option will let cast members know that you would like a room ready as soon as possible, the only down side is that you may not receive specific requests such as location in order to have your room ready. Also, another great feature is to input your mobile number so that you can receive a text once your room is ready.
Stephanie, I wish there was a magic genie button to press that would get that upgrade for you! If you do find one, let me know. ;-) There is always a chance for an upgrade no matter if you are using online check-in or the traditional check-in, upgrades are given based on inventory and sometimes it may just be your turn for some extra magic. Cast members love to sprinkle guests with as much pixie dust as they can, but it's just not always possible. I wouldn't expect to receive an upgrade, but it makes a nice surprise if you receive one. Plus, in my experience it can never hurts to ask.
Thank you for visiting us at Disney Parks Moms Panel, Stephanie! Please come see me again if you have anymore questions or need advice.
Happy Planning!
Mandy