My younger daughter was 2 on her first two WDW trips. I can't stress enough that every child is different, but I can share with you what did and didn't work for mine.
- NAPS - mine never were stroller nappers. WDW was just so many noises and stimulation factors that leaving the parks for meaningful quiet nap time at the resort was the only sensible plan for us.
- WORKING NAPS BREAKS TO YOUR ADVANTAGE - We'd nap break from about 2pm to 6pm (or sometimes a little later) every day. Yes, it's a LONG nap, but it helped get her enough rest so she's be good for TS dinners, evening shows/fireworks, and sometimes evening EMH. Yup- there were a few times when she was in the parks until 1am at that age. Plus, but skipping out of the parks midday- you're missing the parks at peak crowd times.
- RECOGNIZE AN APPROACHING MELTDOWN - While we had a couple where I had no choice, but to weather it since nothing was working to calm her down...most were remedied by seeing it coming and changing our situation/location. Mind you, a lot of hers were over sibling jealousy - i.e. she was 2 and her big sis was big enough to do some things she couldn't. Still, if I could get her out of a situation fast enough, I could minimize the meltdown or at least get her away from the crowds to avoid greater over-stimulation (as well as saving others from hearing the meltdown).
- PLAN LITTLE PLEASANT DISTRACTIONS - I liked to plan in little things that were cute or magical, but also were little things I could do to that would capture her attention positively in lines or meals without disrupting others. Sometimes it was little outfit details or park details...and sometimes it was my fave. My fave was "dusting" my girls. I often travel with fine grade cake glitter. I would dust their hair (usually without them knowing) before leaving the room and might use my phone to take a pic of their scalp while in line so they could see that Tink had secretly paid them a visit and sprinkled them in pixie dust.
- CHARACTER MEALS - Every kid responds a bit differently, but we found that by getting in a good character meal in the morning could save us from the whining and begging for M&Gs while in the parks. Just make sure you have plenty of snacks handy b/c the meals distract them so much and they often don't eat as much as they should. I swear, hunger from failing to eat at overstimulating meals is one of the biggest meltdown factors.
- POTTY TIME - My younger one was still in diapers on her first trip as a 2 yr old, but potty trained by her 2nd two year old trip. No real tips here, but just wanted to point out that it doesn't make a real time or packing difference. If he's in diapers, you'll have all the normal diapers and wipes in your bag. If he's potty trained, you'll have so many spare outfits for potential accidents that you need the same amount of bag space. And the amount of time going to the bathroom is about the same.
- STOP AND APPRECIATE THINGS - since you're like not going to be jumping around from Space Mountain in MK and Everest in AK, use it as a time to appreciate the little details.
- STROLLER - On her first trip, we brought our stroller from home. It was a sit n stand...comfy, but nothing too exciting. On or second trip with her as a 2 yr old, we rented a City Mini Double. She was so much more comfortable and it made a HUGE difference in her mood.
As for the crib, we opted for a different route. I'm pretty sure they'll supply a pack and play, but we had them put bed rails on a queen bed instead.
I'm sure there's more...but this is what I can remember