@Odin
yes...a #### ton to digest, but my suggestions is to break things down based on what you need to do 1st (like hotel) then forget about rides, meals, entertainment till after step 1 is locked in and you can focus on those, b/c there is a lot to look at there.
so, hotels, your right, deluxe's offer better transportation options based on general location. However, there is not a huge drop off to moderate when it comes to the hotel itself. So if you don't mind a bus ride (and 10-20's not 45 minutes) you can be in a really nice hotel for a bit less. You can get a feel for each place by just checking out the WDW web site. They each have their own vibe and theming. IMO the best moderate is Port Orleans, it has such a great feel, awesome grounds, easy boat ride to Disney Springs (formerly Downtown Disney, formerly formerly Lake Buena Vista Shopping Village) and nice soothing rooms. I saw that vs the Caribbean Beach type hotels where (IMO) it is too bright and pastelly looking. If I want Caribbean, I'll go to the Caribbean.
On the deluxe side, there are some great and very different vibe resorts.
The classic ones are by the Magic Kingdom—Grand Flo, Polly and Cantemp/Bay Lake Tower. These are great b/c they fit the 'fireworks from the beach/room" item you were talking about. They do have monorail access, but IMO, I very rarely use it when I'm there except to get to Epcot. Resort Boats are easier or we just walk (if staying at contemp).
Wilderness lodge is considered a MK resort, but there is no monorail, only boat or bus access to the MK. It is a beautiful hotel and lots of people love it. It will also be under renovation for a while as they are adding DVC (Disney time share) rooms. So be aware of that.
Epcot area deluxe has some of the nicest resorts—Boardwalk and Yacht/Beach Club. Both of them are spitting distance to Epcot and Studios. So what you miss in monorail to MK, you make up in access to 2 parks. Plus, the Boardwalk is a great nighttime attraction in itself if you don't feel like doing the parks on night.
Then the is Animal Kingdom Lodge is the sore thumb of resorts. Amazingly beautiful, so fun with the animals grazing right outside your room, but its also the furthest away from the parks and only has Bus transportation.
On the transportation side, pain/pleasure of the WDW transport system is directly related to how busy it is. If you go in a slower season, the busses are usually pretty manageable. Plus, there is also a bunch ofd taxis and Uber on property for when you just don't want to wait for the bus or need to be somewhere quick.
so, really, take the time and research the resorts first. Youtube is your friend here. Lots of resort walk throughs and such so you can get a good look at the vibe, pools, amenities, etc. Also, think about what parks your kids would enjoy the most and think you would spend the most time in—my bet would be Magic Kingdom being your are pretty much 1st timers. So as Acer said, Polly is a great location. We stay at Bay Lake/Contemporary simply for the location and ease of getting to the MK.
We are here, report back if you need any clarification or trying to decide b/t resorts. The rest will fall in place after booking.
quick on the other questions
• 6mos out to start planning is optimal, if not more. There will be benchmarks that will be important to you, like making your dining reservations at 180 days out which is pretty much 6 months. If you don't make your ADRs (advance dining reservations) was soon as you can, you'll find it hard to make those ADR for some popular locations (yes those Character meals).
• For Fast Passes (we will go over those later) you need to make those at 60 days out.
• Dining plan, we do the 1 TS (Table Service), 1 QS (quick service/Fast food) and 1 snack (popcorn, ice cream, bagel) per day and it works fine. 2 TS is a LOT of time in restaurants. if you really need to go to a diner, and it does not fit the meal plan, you can always pay out of pocket for it.
• Wait times: they varry...there is great app you can get for free that will keep you posted of what the waits are like in real time.
• Fastpass, is just a ride reservation time. You pick 3 ride a day, pick the time you want to ride them and you get in a special, shorter line for that ride. You can add more after you use your 1st 3.
hang in there..we will get you through this!!