@STBootleg Awesome!
Yes, there is a lot to digest, but feel free to ask anything. Lots of good, knowledgeable Disney peeps in here willing to lend an opinion.
Fist thing is to find your comfortable budget and work back from there. That will dictate all things from resort choice, on/off site, length of stay, # of park days, etc. Its a tough target to slide into b/c its not so cut and dry—like you you will save $ by staying off site, but then you need to factor in a car rental and parking. Stuff like that.
Also, if its your1st time or have not been in a while, there is no shame in having a certified Diz travel agent book the main part of the vacation for you. Their services are free—they get a commission by WDW—and their job is to keep up with all the discounts and offers out there in addition to a lot of the annoying (to some) nitty gritty details of the vacation. If you go that route, you can still bounce ideas off of us here and get everyone's opinion.
I really only know the on-site resorts, but off site you have lots of good chain-type hotels as well as renting someones timeshare or vacation home. On site, there are 3 categories:
Value: these are your cheapest rooms. THey usually have a big quick service location to eat and are pretty much straight up hotel rooms. But what they lack in overall amenities, they make up in super sized Disney theming.
Moderates: This is your middle tier room. Rooms are still pretty straight up, but the grounds are a bit more sculptured, there is usually a sit down as well as QS dining options and they are closer to the parks or Disney Springs (where you can take a boat vs only relying on the buses). These also offer some special theme rooms like princess or pirate themed ones.
Deluxe: these are the signature resorts, some on the monorail line. They are usually just outside the theme parks and offer the better (to some) views, pools and other amenities. THey often have multiple restaurants and bars.
there is a 4th set of resorts that are on property but not owned by Disney—The Swan and Dolphin. I believe these are Starwood holels, so if you have any SW loyalty points, you can use them there. The difference these have vs other off=property ones is that they have use of the Disney buses and are in the Epcot/Studios area maknig it easier to hit those parks then truly coming from off site.
Once you have your resorts picked out and the prices for those in line, then the rest of the stuff falls in line.
pros/cons to on site vs off site are:
On site:
Disney transportation runs all day/night
Access to the meal plan (and at certain time of year it may be free)
Ticket package discount
Magical Express (free bus and luggage service to and from Orlando Airport)
60 window for getting fast passes
In park purchases can be delivered to hotel
But...more expensive then most hotels.
Off site (timeshares, hotel, vacation homes)
Cheaper
Prob need to rent a car (unless you are driving)
Parking ($15 per day at most parks)
A little more freedom to hit Universal or other area attractions
30 day fast pass window
No dining plan, but off site restaurants are gonna be cheaper
hope that helps to get you started. IMO, I like to use Youtube as a guide. Put some resort names in there and you'll find lots of walk around videos and really see the grounds, pools, etc. Check out Google Maps and see a good overview of the property (pssst.....Its a big place) and see where resorts fall in relation to the parks.
any other questions, give a shout