It does seem like there's a lot of info to sift through, BUT it is not undoable - esp if you enjoy reading about things. Really, the biggest things you have to decide are: where to stay, dining plan or not, dining reservations for any of the sit-down restaurants (and most of these you can take your time deciding over the next few months), and 3 rides you want to reserve each day called FP+ (these you don't have to pick until 60 days ahead of time -- and keep in mind that you can keep changing them up any time you want).
Highly HIGHLY recommend staying on site. Nothing beats the convenience and magical feeling of staying on site. Esp for your first time visiting.
We love the value resorts - all of them. Check them out online and see if you think they'll work for your family. Although you will spend time at your resort, most likely you will spend little time in the room itself.
What I've done in the past to decide if I wanted the dining plan or not was to go through 1 day in my mind and pick out what I wanted to eat for each meal and snack and add up the cost, multiply over the number of days, etc and compare with what it costs to add on the dining plan. allears.net has menus for all the restaurants and snack places, so you could do that easily. Depending on how your family likes to eat, you may or may not save $ with it. Keep in mind that you can bring meals and snacks in to the parks with you.
You are correct-- if you are staying at Disney, then all your eating will be at Disney (whether in the parks, at your hotel, or at Downtown Disney). And actually, even if you stayed off site, you would most likely do all or most of your eating at Disney also unless you cut your park days short and left to go eat out by your hotel. Another highly HIGHLY recommend for staying on site-- keeping all of your activities on site is very convenient!
If you want to eat at Be Our Guest or some of the other most popular TS ("table service" or sit-down inside) restaurants, you would need to make those reservations right away -- snap up whatever you think would work best. But most places you'd be able to take your time over the next few weeks and months deciding about. For everywhere else to eat (QS, or "quick service" which are counter-service places, some have inside seating and some have outside seating; plus there are plenty of snack stands also), you can just decide on the go-- see what's nearby when you get hungry.
Don't let the numerous threads on FP+ ("Fast Pass Plus," or ride reservations) scare you away-- it basically boils down to being able to guarantee yourself a little to no wait time for 3 rides per day by picking them ahead of time. And if your trip is in November, you won't be able to do this until 60 days ahead (whatever date in September is 60 days ahead of your check-in day), so plenty of time to figure that out. When you do get to that step, I highly recommend easywdw.com for making those kinds of decisions and seeing what crowd levels are on any given day. But also- especially if you wind up going during a lower crowd time in November- you will be able to switch most of these around as many times as you want, and even when you are actually in the parks. For example, a few weeks ago we had run a little late arriving at Disney on our first day and I realized we weren't going to be able to make our FP+ times for that day. So as we were getting on the bus to go to the parks I pulled out my phone and switched them around for an hour later - it was quick and easy.
If you are the type that would rather let someone else set up these kinds of things for you, then go ahead and use a TA for your first trip. But if you are the type that likes to do a little investigating of your own and be in control of all of it along the way, don't be scared off-- there are not many things you "need" to do past the initial hotel reservation, and there is plenty of time for you to look into as many details as you want between now and your trip.
On the DIS there are a lot of people that are uber-planners and make spreadsheets of what to do every minute of every day on vacation, but there are also plenty of people who relax into their vacation with little to no ahead of time planning. I find that how much fun people have seems highly dependent on what kind of attitude you go on vacation with -- and I think if you are determined to have fun soaking up the magic, then nothing will get in your way of that.
Good luck & have a magical time!
welcome to the Dis!
