again, congratulations!
As you know, we had our thirst last July ... and then went to Disney in August so not sure I am the best one to give advice
Actually, one tip I do have is to play around with different car seat configurations, etc. and some stores will let you take the floor models out to your car to see how they fit. By doing that we figured out a set that worked fitting three across the back of my sedan (Kia Optima) which I didn't think was possible.
Only other thing I can say is we had a lot of people telling us going from 2 to 3 wasn't a big deal, but I have found it kinda has been - it's been great but also can be challenging as we now have to play zone defense at times.
Oh, we've also found Disney Infinity can be a good distraction when we need to spend more time with the baby
oh, and I think your plans sound pretty darn good. We enjoyed the 'Ohana dinner - though not a fan of the new lettuce cups they have. But the wings and pot-stickers are great and the meat - especially the pork - was much better than it has been in the past. And of course the bread pudding is amazing!
50s prime time is great too - hopefully you get a good CM waiting on you (most are at least pretty good but some better than others) .... assuming you want to have fun with them that is. The chicken is really good and the sample is a good option too. The desserts are pretty big there.
Have a great trip and congratulations again, again