We've had luggage transferred our last two trips and had no issues. The day before you are going to check out, call Bell Services and explain what you are going to do and how they would like to do it. Some of the resorts (POFQ, for example) wanted us to pick a time for them to get the bags. Other resorts (BWV, for example) said to call 20 minutes before we wanted them picked up. Still another resort (POP) said just to leave them in the room and they will take care of them.
Then, when you get to the other resort, you can call their bell services and if they are there, they will be delivered.
Hope that helps. Any other questions, let me know and I'll be glad to answer.