I'm going to start off by saying I am no Disney expert. Far from it. We didn't do a lot of research in to going-other than picking a date and choosing rides for our FP+. So, while these are my opinions, I suggest you do some additional research on what might be right for you.
When to go
Since S isn't in school yet, we were able to take advantage of going during an off season. Late January/early February and September (after Labor Day) seem to be the best times to go to avoid the crowds. There are probably other times, but I have been during each of these times and it has been nice.
Staying on or off Disney property
We prefer to stay on Disney in a value resort. Read about Pop Century here. We flew and took the Magical Express from the airport to the hotel. They delivered our luggage and we didn't even lift a finger. Now, if you are flying in late afternoon, I suggest you not use the luggage service--or pack your pjs in your carry on. Bedtime was later than we wanted the first night because we were waiting on luggage, but hey, it's vacation. And since we were with a younger child, we were needing an earlier bedtime than usual.
Also, staying on Disney gives you the opportunity to use their transportation to the parks (or not). Depending on your hotel, you could use the bus, boat, or monorail. I've seen comments about the bus being too crowded, etc. It wasn't a problem for us, and yes, we stood on a few rides.
Our Quick Service plan was included in the package we purchased through Disney World. Was it worth it? To us, yes. We liked having everything paid for upfront. But, portions are huge. We had some leftover meals that we used to purchase snacks and cookies bring home. If you get the table service plan, your Character Meals are included in that. The difference between Quick Service and Table--basically if you have someone bring you food, then you are Table Service. Quick Service is kinda like fast-food. We had 2 meals & 1 snack/day per person. We packed breakfast bars and since we had free drinks at the resort (in the refillable mugs), we just ate in the room most every morning. And you aren't limited to follow the meal parameters. You basically get a lump sum and can use them however you want (all in one day, ok!).
If you are staying at a Disney resort, you will have a Magic Band. These bands are your lifeline. You use them to open your room, gain admission to the park (plus scan your finger), use of the Fast Pass+, and pay for food (plus PIN code). We also attached our credit card to The Professor's band so that he could make purchases in park (Minnie ears, etc) without having to carry a credit card or cash. If you are purchasing food or other items, there is a PIN code required--so that way if someone else has your band, they can't make purchases with it unless they know the code. We would let S swipe her band, and then we would type in the code. She felt big--like she was paying for our food.
We customized our bands ahead of time and were able to pick colors. If you decided not to do this, they are a generic grey. However, the Disney gift shops sell things to spruce up your bands, if you decide to do that.
Fast Pass +
If you've been to Disney, you may be familiar with the Fast Pass system. You would scan your admission ticket and then get a paper admission to a ride for a later time. That way you wouldn't have to stand in line. Well, the paper machines are gone. Now there is FP+! You are limited to 3 FP+ per park per day. If you are a Disney guest, you can reserve your FP+ times 60 days in advance of your arrival. These are loaded onto your Magic Bands and you are able to make changes as much as you like. If you are not staying at Disney, from what I understand, you will need to go to the FP+ kiosks with your admission ticket and choose rides on-site. Be warned--there are lines to the FP+ kiosks. We downloaded the free My Disney Experience app and was able to make our FP+ changes with that and didn't have to stand in line at the kiosk. I recommend you do that--it was such a time saver!!!
Disney sells autograph books that you can buy there (park, hotel, Downtown Disney) or you can even make your own. We didn't do an autograph book. We had the characters we met sign a picture mat. I'm going to let S pick her favorite picture and then frame it with this mat and hang it in her room. And I have to thank Pinterest for this idea--totally wan't mine. I kept it between cardboard so it didn't bend and then that inside a plastic bag so it wouldn't get wet if we were in the rain. The Professor carried it in his backpack.
I searched quite a bit online for the best time to go (value/low crowds) and what attractions needed a FP+ reservation. Here are a list of the websites and FREE apps that I used.
1. Morgan Crutchfield was such a big help. I met her through a friend on FB & Twitter and she answered so many questions for me. She has a website DVC Central, a FB page here, and you are welcome to tweet her here. Seriously--she knows EVERYTHING!!!!
2. Easy WDW--this website is where I found the crowd calendar that we used. Also lots of useful information.
3. WDW Prep School--this had lots of information, touring guides, etc. A great resource.
4. My Disney Experience--I also downloaded this as an app. It had all of our trip information on it, where I managed our FP+ reservations, ride wait times, character times, park maps, photos--everything we needed before, during, and after Disney. We also ordered personalized park maps from this site too.
5. SeeYaReelSoon--Joe and Ashley, I don't even have words. I love them so much. After we booked tickets, I wanted to show S what Disney was all about, so I YouTubed it. After scanning through what seemed like a million videos, I found these two. And y'all, we were hooked on them. They release a new video every Wednesday night--sometimes they are just at their house answering questions, but a lot of times they are vlogging in the park from a recent trip!! We get to go on rides with them, visit characters with them, and eat with them. S calls them the funny people at Disney because they are so cute and make us laugh. And they have a website with a Dining Calculator and other tips.
6. DIS discussion board--I also downloaded this as an app on my phone. I never joined or left a message, but it was fun to look at and see what people were talking about.
There are quite a few things I didn't touch on. We didn't purchase the Memory Maker photo package--we just took our own pictures or asked a Cast Member to use our camera. The pictures the photographers took of us are able to be purchased, if we choose. We also didn't use a stroller. S walked the entire time we were there. I'm very surprised because Disney is ALOT of walking--especially for an almost 5 year old.
Also, Disney World is expensive--even if you go off season and stay at the value resorts. We had saved money to go, but for our next trip, I am going to pay a little at a time. Our local Kroger sells Disney gift cards that can be used toward your stay. And certain times of the year, I get 4x fuel points for gift card purchases. Ch-ching!! Paying for Disney and getting a gas discount. Woo Hoo!!
I hope you enjoyed our journey to Disney World!