Before you go, make copies of the Magical Express booklet, vouchers, etc. for each person or group. If you arrivals into Orlando differ by just a few hours, no problem, no need to notify.
As soon as you get there, either at the airport DME welcoming area or at your resort, each person arranges the trip back to the airport.
Double checking required for all DME guests regardless of homebound schedule: Morning of the day before the day each person leaves, he should get a paper with his DME reservation back to the airport. If this paper is incorrect or does not arrive at the room, that person needs to go down to the front desk and make any needed corrections. It is necessary to get the new confirmation as soon as that is available and this could mean missing rope drop or having to return to the resort that afternoon to get the paper.