Have you considered that you may not have a room before your luggage arrives anyway? Most luggage transfers are done between 3 and 5, when most rooms are assigned.
Don't know what you have planned that day but we always plan to be in the parks till 5:00, that way, we never need our bags till they are moved.
We did a 4 way split stay in January and it was so nice to just let them do it all. Only one out of the 4 was the room ready early.
Neither. Both services are on demand.
Sounds like your day is a perfect one to let Disney do the moving. What time is your Dinner?