DME is specifically set up so that you DON'T need to be in your room when your checked luggage arrives. In fact, Disney even pre-tips the Bell Services staff for you, so they don't lose out. When my luggage arrived, I was in the pool with my kids, and when we got back from the pool the luggage had "magically" appeared. I think DME luggage delivery would pretty much stink if you had to wait for it -- if it was that way, I would've taken the luggage on the bus with me. I can't imagine having to sit around the room and wait when the last thing I'd want to do is DO NOTHING. And by the way, if your DME driver handles your carry-ons for you (they can be stowed in the cargo bay if you like), it would be appropriate to tip him/her.
Now, on your trip home it's a different story. If you have Bell Services pick up your luggage, you should tip that person appropriately. And unlike your luggage delivery TO your room, your luggage pick up FROM your room is NOT automatic -- if you want it, you have to call Bell Services to request a pick up. The driver will load your bags into the cargo bay (assuming you're not flying a "participating" airline), and again if the driver handles your bags it is customary to tip.
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