We always take our luggage as carry-ons, and in that case, our luggage stays with us until we put it under the bus for transport to WDW. Then we collect it before we go check in. Our room has always been ready, and I am not sure if that is b/c of early online check-in, or if it has been a fluke, but we just take our luggage to our rooms. If it hadn't been ready, we would have just left it there with them, and they hold it until the room is ready. My parents once did checked luggage, and theirs was brought directly to their room after they had already arrived and gone into the parks. When we did a split stay in May, we had our luggage transferred from one resort to another, and it took a while to get to us there. We came back from the parks and needed naps. Since the luggage was nowhere to be found, I stripped off my sweaty clothes and napped in my underclothes. It was actually a lovely nap. Our luggage was then delivered straight to our room.