First trip with a Toddler, so many ???s

the only part I'm qualified to answer is about carseats. This is also going to be our first time to disney.

I've done it with and without the carseat.
Try using a little rolling luggage cart with a bungie cord for the carseat.
1st is for safety. If the plane hits rough weather or an airpocket the seatbelt will not hold them. They do sell some new straps that may also work for the safety concern.

2nd ds is really comfy in his carseat. Once I bought one so I wouldn't need to lug it on the plane. The quality was not the same.
 


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