We do split stay often. We just absorb the cost of using taxi or uber, rather than waiting hours for luggage to arrive. I heard to not expect luggage to arrive till something like 4 or 5 in the afternoon if you send the luggage with Disney. DEFINATELY pack a day bag! We typically try to check into 2nd part of split stay early. We will have breakfast and make our way to the park. We have had good success having our room ready relatively "early" that way.