Hi Stephanie!
You can request a connecting room at the Walt Disney World Resorts but it is only a request and not a guarantee. That said, my family and I have always received connecting room whenever we requested them. By the way, since it is your first visit, I recommend picking up the book "The Complete Walt Disney World" by Julie and Mike Neal. It's a fabulous book, especially for first timers; it has just the right amount of information without being overwhelming. It's also a beautiful book, full of color pictures. It will give you a great idea of everything there is to do at Walt Disney World.
With regards to picking a dining plan, I recommend visiting the independent website AllEars.Net. There you can look at the menus of the different restaurants at Walt Disney World. The team at All Ears does a great job keeping their information up to date with all of the changes at Walt Disney World. With the menus in hand, you can get a feel for how much each meal will cost based on how your family normally dines and what each member of your family might order. You can then compare that cost to the various
Disney Dining Plans. Only by doing the math can you figure out which is best for you. Some guests save a lot of money by being on a Disney Dining Plan, while others save only a little, and some guests actually spend more!
Good luck planning your magical Walt Disney World Resort vacation and write back if you have any more questions!