Hello Megan! Welcome to the Disney Parks Moms Panel.
I book my family's Walt Disney World Resort vacations well in advance. Part of this has to do with my personality but more importantly, the Endless Magic of a Walt Disney World Resort vacation makes the process of altering or canceling a reservation straightforward and easy.
The good news is that in addition to altering based on changing your mind, another added benefit in securing a Walt Disney World Resort room early is that you can still take advantage of
any future or better value Special Offers that might be available closer to your travel dates (by Modifying your Reservation).
As far as making an additional reservation, I am sure that as long as you are willing to pay the required deposit (full cost if purchasing as a package, a percentage if room-only) then there would be no problem in booking an additional resort hotel room. Be very careful to
cancel the superfluous reservation according to the cancellation policy to avoid being charged for both reservations. If you have difficulty booking the 2nd reservation online (due to linking Guests), then I suggest you speak with a Cast Member at Guest Services by calling (407) 934-7639.
I understand your desire for 2 Walt Disney World Resort reservations to avoid the possibility of having a room sellout before you reach a decision. In the past, I have maintained only 1 reservation and modified said booking to take advantage of Special Offers or change of plans. To "Modify your Reservation",
sign into your My Disney Experience Account, select the appropriate booking under My Reservations and select the tab "Modify Reservation".
Good luck with your decision!