Hello Michael - great to hear from CT! I bet you wish you could head to FL now to get away from the snowy winter! Anyway, you've come to the right place - we are all happy to help your Walt Disney World vacation. I have to warn you that we have limited space when answering questions so you may need to ask follow-up questions so we can help you further. Ask as many as you need to. It would also be helpful to know the dynamics of your family (i.e., 2 adults, 1 child; 1 adult, 2 children and the age/gender of the children).
As far as what resort to choose, it depends your budget/preferences. There are deluxe, moderate and budget resorts. Once you decide on your price range, your next questions you'll want to answer are what area of WDW do you prefer to stay in and what resort theme. You can start your initial research on the
Explore the Resorts page. I can help you further once you decide what level of resorts you want to stay at or if you have a couple in mind, let me know and I can help weigh the pros and cons for you.
When deciding if a Disney Dining Plan is right for your vacation, you'll need to have an idea on what type of dining you'll be enjoying - mostly table service, mostly quick service, a combination of both. Do you have any must-do dining, etc. Once we know the age/gender of your child(ren) we can offer some great suggestions and we'll help you decide if the Dining Plan is a good idea for your vacation. I will say if you are planning at least one table service meal each day, the Dining Plan can probably save you money. It's also very convenient to be on a plan as well.
Check out the link above and send me a few more specific questions and I'll be happy to help further. We'll need to address the parks, tickets in a separate question due to the limited space. Your vacation is going to be awesome!