It don't matter. We are getting in a day before the rest of our family as we have to fly from Germany. We are then going to stay Hyatt Regency and get on the bus the next day. So long as you fly and are staying on the Disney property you are good to go. Take your time and board at your convenience. There is always a next bus.
Splitting hairs. So long as you present yourself at the Magical Express welcoming area (at MCO) no matter how or when you got there, have an advance DME reservation, and are staying on the Disney property, you are good to go.
Just to clarify: On your way to the resort you do not have set bus time. On the way back to the airport, you do. That time, you have to make. There is no next bus they will automatically put you on.
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