Hi, Amber!
The servers at Walt Disney World have encountered every type of travel party, so they will be happy to do whatever you want with the bill at the end of your meal. You can do separate checks for each guest, split the check in two, get one check but tell them to split it between two credit cards, or whatever combination you can come up with. You can pay for your meal/tax/tip with cash, credit card,
gift card, or charge back to your Disney resort room. I just had dinner a few weeks ago with a group of friends, and the lovely server at our
Disney Springs restaurant was happy to give 6 separate checks, add on
Annual Pass discounts, and have each of us pay with our own methods. Really, there is not much you can come up with that they cannot do for you!
That leaves just one thing for you to worry about: Where to eat! There are so many great restaurants to choose from in Walt Disney World! I suggest making
Dining Reservations ahead of time so you have the time and place worked out, and you can tell everyone in your party the plans. You can all meet about 10 minutes prior to your reservation then have a enjoy a wonderful meal together. It sounds like a super fun way to spend time with friends and family!
Cathy