Transportation - We flew nonstop from Detroit to MCO. She was still on my lap (FREE AGAIN!!) and it was 'ok'. (Warning - not all airplanes have changing tables in bathroom!!

)
Resort - Haha. We actually had to switch halfway through. We stayed at both ASSports and ASMovies. I have been there before, and although I would love to stay at a moderate/deluxe, there is no way I could have afforded it (or justified spending more money). I like them anyway, so no problems.
Naps - we tried twice to take a nap in the stroller. 1st time was only about 45 minutes. The 2nd time was about 1 1/2 hrs. It was just easier to go back to the room and make sure she slept good. Again, I didn't want to get her tired, because that would make her cranky and w/ only me there....didn't want that to happen!
Meals - that is the only thing I would change about my DD - she doesn't really eat, except for fruit. (Finally getting a little better in the last week or so). Because I was on a budget, I got a kids meals a lot for me, drank water. I brought down cereal, juice, etc in our luggage so I didn't have to buy that.
She loved all the parks. MK - that's a given - Fantasyland. She really enjoyed the playgrounds and picking up the pixie dust on the floor. She loved all the music she heard on Main Street. Epcot - the interactive water fountains - she could stay there for a LONG time! The lighted pavement at night. The hot air balloons in the Land (on the ceiling for decoration!). DHS - Playhouse Disney was AWESOME!! Little Mermaid. AK - the ducks and the birds were her favorite. We loved walking around the tree of life and looking at all the animals. She was in such awe the 1st half of the trip. I basically just did everything I thought she would enjoy. It was great. You literally make all the decisions. You don't have to decide where to go, where to eat, etc. You just make the decisions. It was very relaxing actually! I laughed because I would hear an 8 yr old whining about something or complaining and I thought - gosh, being almost 2 is great!
If I could recommend one thing - to go for 8 or 9 days. It makes it so much easier having the couple extra days, you can see more and go at a slower pace.
Also, be prepared the 1st day or so YOU will be sore. My mom is in a wheelchair, so normally DD sits on her lap. I didn't realize how LONG the lines were to walk through (ie Small World, Peter Pan, PIRATES!!

has a REALLY long line to walk through)! I usually tried to carry her, because I didn't want her to get so exhausted walking that far, and she was a little nervous. My legs were tired from lifting her so much. (AND I work where I lift heavy pkgs for 3 hrs a day!)
Since you have been there before, you probably know NOT to wait in lines. Either get up early, get a fast pass or go by. We NEVER waited in a line and that definately helped.
He may or may not like the characters. In August my DD didn't mind the characters. In January (4 months later!) she was terrified of them!! (Not so much the face ones, but Mickey and all the others).
Buffets are tricky to eat at. The only time I got stressed out the entire time was when we ate at Chef Mickey's (our only buffet this trip). I think it was because I had to bring her up with me to get food, I was trying to document everything - video AND camera plus get autographs in her book and on her t-shirt. Way too much. This next time, I need to pick 1 thing to do while at a buffet, not try to do ALL things at once!
Get the photopass CD. I am such a picture person. It was so much fun to get almost 500 pictures taken. It was so much easier to get a couple done by them, rather than giving someone my camera everytime. I would also tell them I am getting the CD and ask them to snap away!
Let me know if you have other questions. Start planning! It's awesome.