Hi Kathy,
Boy are you a real sweetheart for planning a trip for 41 people!
Your questions are very broad but I can give you some general guidelines I use when planning a trip for a large party.
First, are you willing to take the children out of school? If not, then the summer or holidays are your options. The summers will be hot and humid. The holidays will be crowded. If the children are not on a traditional school calendar (September-June), you may be able to schedule vacation during the fall or spring. I love Disney in October, and it would be my first choice for the temperature and the
Epcot International Food and Wine Festival.
As for where to stay, figure out a rough itinerary regarding which parks you will be touring. If you are concentrating on only certain parks, then stay closer to those parks. It also helps reduce your transportation time and allows you to come back and forth from the resort if you need a break. There are wonderful resorts at all price points within the Walt Disney World properties. You may even want to book a few
villas which hold 12 people and have full cooking facilities to save on meals.
I would have a conversation with your family about how much time you want to spend together - everyday, every meal? This is where it can get challenging to coordinate timing of meals. You will need to book your Advance Dining Reservations as soon as the 90 day window opens and mention that you are a Grand Gathering with more than 8 people. This will help them coordinate tables for you. You will fill half a restaurant in many instances.
Have a magical journey!
Beth