I think DD's first WDW trip at age 2 was my favorite WDW trip. She is 9 now and we have been every year since. At age 2, everything was real and magical to her and she spent almost the entire week with a huge grin on her face.
I don't think you can predict how a child will be or react at WDW until you are actually there. Flexibility is the key when they are that age. FP+ can make that really hard, but it is something we have to live with now.
My biggest surprise was that DD who was a "spirited" toddler to say the least, was a perfect angel almost the entire week at WDW. The only major meltdown I can recall was when we tried to enforce the afternoon break our first full day- we quickly found out that did not work for her at all. She was livid we made her leave the park, and she was an angry toddler who sulked behind the curtain in the room and refused to nap for the next 2 or 3 hours until we finally just gave up and went back to MK where she immediately got a huge smile on her face and crawled in her stroller and took a nap for over an hour. After that (and pretty much every year since) we stayed in the parks open to close -just like we did before DD- and in the stroller years, she would nap in the stroller when she got tired. That worked well for DH and I because we would take turns riding the rides she could not or would not ride while she napped. You have to figure out what works for your kid. Things we found:
1. If your kid is not a morning person, they are not going to suddenly turn into a morning person at WDW- especially if you have even a one hour time change. Pre-park opening breakfasts sound great in theory. If you have a child who is a night owl, and not a morning person, pre-park opening breakfasts are a nightmare. We found that out the hard way. Not only was DD cranky having to get up early enough to get to the pre park opening breakfast (don't forget you have to leave your resort an hour or more ahead of your ADR time if you are using Disney Transport), she actually fell asleep at the table during breakfast at Tusker House and did not want to wake up to greet Mickey. It took about an hour after breakfast before she was her pleasant energetic self. Getting to the park at rope drop is hard enough- save yourself the misery and plan on having one of you go to CS and bring breakfast up to the room for the kid, or have groceries in the room. If you have a morning person kid, then pre-park breakfasts can be fun. On the flip side, DD is a night person so staying in the parks until almost midnight at
MVMCP was fine with her (at age 3 we dragged her out at 11:30 p.m. throwing a fit because she wanted to ride Barnstormer again--- this was after she had ridden it 13 times in a row- mostly without even getting off- and DH and I could not take even one more time). If you have an early to bed total morning person- nights could be issues for you.
2. As stated above, the mid-day break does not work for everyone. Don't be convinced by the boards that you have to take one. It may work great for you, it may not. You said that you did not think your DS would nap in the parks. He could surprise you on that. WDW can wipe them out to where they can fall asleep just about anywhere. DD never set foot in a stroller after reaching the age of 12 months- not at the zoo, the mall, or anywhere that involved a lot of walking. She wanted nothing to do with strollers. Once she realized how big WDW was and that it would get her places quicker, she hopped right in that stroller. DD quit taking naps on her third birthday. If she slept even 10 minutes after that, she would be up until midnight or later. At WDW, she took stroller naps every day at age 3 and 4, and maybe even at 5. Also, if she seemed tired, but claimed she wasn't, we would find an excuse to get her to sit in the stroller and to walk around a bit and she would fall asleep. It is a whole different ball game there.
3. The best TS meal for us when DD was a toddler was lunch. We would go full speed from rope drop to lunch, then lunch would wind her down enough to get in the stroller and take a nap after lunch. It would also give us a good break and rest to rev up again for the rest of the day. Even now, we don't take afternoon breaks, and lunch TS is great to give DD a rest and get her fired up to keep going the rest of the day. When DD was little, dinner TS was a little rougher, by evening she would be tired and then she would be restless and wilder at dinner. Also, once she sat for that long the tiredness might set in and then she would pretty much be done for the night. If we did our TS for lunch and then just did a quick CS for dinner, she would keep going strong until closing. Now that she is older she is fine at TS dinner, but lunch still works great for a break.
4. The non-park day. Lots of Disers swear by a non-park day. DD would have none of that at age 2. Once she was awake, she was standing at the door of the room with her stroller telling us to hurry up to get her to a park. A non-park day would have been a disaster. We went to the parks all day every day for a week. We are a high energy family. Other families (like my BIL/SIL) would not do well with that. All bets are kind of off with the changes at DHS right now, but we have always found that DHS is a great park for when you have been going strong for several days and are tired, because it is very show heavy. It is a day with a lot of sitting for us.
5. Give your kid the flexibility to take the time to smell the roses. The littlest thing that you probably would have overlooked, might suddenly become the most interesting amazing thing to them. If your kid wants to ride the boat in Mexico over and over and there isn't much of a line, let him (we imposed a 5 time in a row maximum). Toddlers like repeats which FP+ can make hard. I remember DD cried when Small World ended the first time she rode it because she loved it and did not want it to be over. So we got in line and went again. I know for DD, Peter Pan was her absolute favorite when she was under 5. That was pretty much the only thing we FP at MK, and we might FP that 4 or 5 times in a day. Every time our wait time to get a new FP was up, I would just grab a new Peter Pan FP. FP+ makes that impossible, and also even makes the standby lines for things like Small World longer so you will have to work around that. WDW is a lot slower with a preschooler, but it is wonderful seeing it through their eyes.
6. Be prepared for them not to match your expectations. I was so excited for that moment when DD would see the castle and be in awe. She walked in MK, spotted Pluto, and could care less about the castle. She then happily stood in line with no complaints (and patience is not her virtue) for 20 minutes waiting for Pluto and then threw herself at him and held him as tight as she could for a long time. There went all my rope drop hit certain rides fast plans, but I wouldn't change that moment for anything. Also what we found was that DD was a character nut, and remained that way for years. She was far more interested in meeting characters than rides. There was a day when she was 3 or 4, that we went from character line to character line the entire day at MK and rode 2 rides. That was not DH and I's idea of a great day, but she claimed it was the Best. Day. Ever. at MK. Of course, your DS may not like the characters- you can probably gauge that by seeing how he reacts to Santa the Chic-Fil-A cow etc.
7. If he is a picky eater, Garden Grocer is your friend. We ordered from them every trip and had groceries delivered when we arrived at the resort every trip until DD was 6. It was great to have breakfast and other food items in the room we knew she would eat.
8. No matter how unique your stroller is, there will be one like it. Tie big crazy ribbons on each side of it, so you can spot it, and so someone else won't take it by mistake.
9. Be sure they get plenty of snacks and drinks. Using all that energy can make them hungry and thirsty. We quickly learned if we saw DD getting cranky, it was usually because she was hungry. A snack would immediately improve her mood. (I'm kind of that way too!)
10. A trick we learned was that for long character or ride lines, DH would give her a little box of raisins. She would eat the raisins one by one and then play with the box for quite a while. It would help pass the line time. If your DS doesn't like raisins, maybe you can come up with a different snack or activity to help in the longer lines.
11. Boardwalk should be great because you can walk to EPCOT and DHS from there, so you won't have to fold a stroller on transportation or rely on the transportation. Be aware though that clown pool of theirs definitely scares some kids- in November it may or may not be warm enough to swim.
Have a great first kid trip!!!